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[ CAS No. 135575-42-7 ] {[proInfo.proName]}

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Chemical Structure| 135575-42-7
Chemical Structure| 135575-42-7
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Product Details of [ 135575-42-7 ]

CAS No. :135575-42-7 MDL No. :MFCD28168025
Formula : C50H80N8O17 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 1065.21 Pubchem ID :-
Synonyms :
L-688786;Hydroxy Echinocandin

Safety of [ 135575-42-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 135575-42-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 135575-42-7 ]

[ 135575-42-7 ] Synthesis Path-Downstream   1~85

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  • C64H89N8O22P [ No CAS ]
  • 4
  • [ 2002-24-6 ]
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  • C52H85N9O17*ClH [ No CAS ]
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  • [ 144539-82-2 ]
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  • 9
  • [ 135575-42-7 ]
  • C50H78N8O16 [ No CAS ]
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  • [ 135575-42-7 ]
  • [ 100-51-6 ]
  • C56H77N7O16 [ No CAS ]
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  • [ 135575-42-7 ]
  • C50H80N8O17 [ No CAS ]
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  • [ 135575-42-7 ]
  • C50H78N8O16 [ No CAS ]
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  • [ 173305-56-1 ]
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  • [ 135575-42-7 ]
  • C50H79N11O17 [ No CAS ]
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  • [ 135575-42-7 ]
  • C52H83N9O18 [ No CAS ]
  • 19
  • [ 135575-42-7 ]
  • C52H83N9O18S [ No CAS ]
  • 20
  • [ 135575-42-7 ]
  • C52H84N10O18 [ No CAS ]
  • 21
  • [ 135575-42-7 ]
  • C53H86N10O18 [ No CAS ]
  • 22
  • [ 135575-42-7 ]
  • C54H85N9O20 [ No CAS ]
  • 23
  • [ 135575-42-7 ]
  • C54H85N9O19S [ No CAS ]
  • 24
  • [ 135575-42-7 ]
  • L-731,373*HCl [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Example 3; Compound of Formula III; A mixture of <strong>[135575-42-7]pneumocandin B</strong>0 (1.80 g, 1.69 mmol), phenylboronic acid (0.433 g, 3.55 mmol) and THF (20 mL) was stirred for 16 h at rt. The solvent was removed in vacuo, and the residual material was dissolved in THF (50 mL). This process was repeated twice, and then the powdered residue was dried at 50 C. in vacuum for 19 h. The powder was dissolved in anhydrous TMF (75 mL), and N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA) (1.3 mL, 4.89 mmol) was added. The mixture was stirred at ambient temperature for 1 h, and cooled to 0 C. A solution of borane-THF complex (1.0 M in THF, 10 mL, 10 mmol) was added during 5 min, and the mixture was stirred at this temperature for 16 h. Aqueous hydrochloric acid (2.0 M, 9 mL, 18 mmol) was added, and the reaction mixture was stirred at 0 C. for 2 h. Water (100 mL) was added, and the product was isolated by chromatography on a 21 mm C18 column, using 26% acetonitrile/74% water as eluent, after washing the column with 15% acetonitrile/85% 0.014 M HCl after load. The rich cuts were pooled and freeze dried after removal of the organic solvent. Yield: 1.0 g (57%) of the title compound as the HCl salt. Purity, HPLC: 96.4%.
  • 25
  • [ 135575-42-7 ]
  • C52H87N9O16*2ClH [ No CAS ]
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  • [ 144476-68-6 ]
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  • [ 138540-61-1 ]
  • 39
  • [ 135575-42-7 ]
  • [ 138540-62-2 ]
YieldReaction ConditionsOperation in experiment
> 90% Purification / work up; A column was prepared containing the N-beta-alaninamidopropyl silica stationary phase; methods for preparing this stationary phase were presented in Examples 1 and 2. The column used was 250 mm long×4.6 mm id, and contained one propylamide moiety bound to an aminopropyl moiety bonded to spherical silica from ES Industries which had 5 mum particle size and 60 pore size. The experiment was similar to that described in Example 8, but the stationary phase was significantly more retentive than most of the others evaluated, and so a stronger mobile phase (75/17/8 ethyl acetate/methanol/water) was needed to completely elute Pn B0 from the column. The results may still be evaluated against the control as illustrated in FIG. 6. A chromatogram obtained from the run on the N-beta-alaninamidopropyl silica bonded phase is shown in FIG. 10. It is important to point out that the large solvent front peak normally observed in the proline elution method system appears diminished. Another difference is that the key impurities that elute at the leading edge of the main Pn B0 peak are well resolved. Several fractions were collected from 6 to 13 cv. The fractions were analyzed by both normal and reversed phase HPLC. The analytical results indicated that the early eluting analogues such as Pn E0 and Pn B5 were clearly resolved from Pn B0. These impurities were mostly contained in the fractions that represent 6 to 8 cv. Results of the normal phase analysis indicate that most of the Pn C0 was resolved into the fractions that represent 11 to 13 cv. Fractions that represent 8 to 11 cv (shown in FIG. 10) could be combined to give a pure rich cut with >90% yield. A low level of the ring-opened degradate was detected in the rich cut fractions. This is a potentially superior stationary phase, since its retentivity allows use of a mobile phase for elution which is very similar in solvent strength to that of the feed solvent mixture, which results in very stable chromatographic performance.
> 90% Purification / work up; Amide-80 bonded phase was obtained as a 250 mm long×4.6 mm id column (10 am particle size, 8 nm pore size, spherical) from Tosoh Biosep LLC. A separation using the same feed material on a bare silica column equilibrated with proline-modified mobile phase was performed as a control, using a W. R. Grace/Davison silica gel Grade-631 column (250 mm long×4.6 mm id, 16-2(Tm particle size, 60 pore size, irregular) supplied by Princeton Chromatography. The mobile phase composition for both runs was 88/917 v/v/v ethyl acetate/methanol/water (e/m/w); the proline-modified mobile phase also contained 0.12 g/L of L-proline. All solvents were HPLC grade from Fisher Scientific. Proline was obtained from Ajinomoto (Japan). A partially purified preparation of Pneumocandin B0 (Pn B0 crude) with a purity of 61.9% was used to prepare the column feed. The methods for preparing Pn B0 crude are given in U.S. Pat. Nos. 5,202,309, 5,194,377 and 6,610,822. For the Amide-80 run, the feed solution was prepared by dissolving Pn B0 crude into a 75/20/8 v/v/v mixture of ethyl acetate, methanol and water; the concentration of Pneumocandin B0 in the feed solution was 45 g/L. For the control run, a 75/17/8 v/v/v ethyl acetate/methanol/water feed solvent mixture was employed, with 1.5 g/L proline, and 45 g/L Pn B0. Before use, the columns were flushed with 10 column volume (cv) of methanol and equilibrated with 10 cv of the mobile phase. For each injection, 1.2 mL of the feed solution was injected (representing 15 g/L bed). The mobile phase flow rate was 0.5 ml/min. For each run, fractions were collected and analyzed to assess the quality of the separation. Each injection was repeated to ensure a consistent elution profile. For the run employing proline-modified mobile phase, 480 mL of the proline-containing mobile phase was pumped through the bare silica column prior to the first injection. Analytical Methods: For each run, fractions were collected and analyzed by reversed and normal phase HPLC. The samples were analyzed on an Agilent HP-1100 analytical HPLC system. The reversed phase HPLC was used to quantify most species, except for Pn C0 which co-elutes with Pn B0 in the reversed phase method. The normal phase HPLC assay was used to determine Pn C0. Measurement of Pn C0 The amount of Pn C0 was determined by normal phase Pn B0 assay, an isocratic HPLC method, which employs a YMC silica column (SL12S05-2546WT) with a particle size of 5 mum and a pore size of 120 . The column was 250×4.6 mm i.d. and maintained at 25 C. Elution was isocratic with 84/9/7 ethyl acetate/methanol/water eluent. Flow rate was 1.2 mL/min, and detection was by UV absorbance of 278 nm. Product samples required no special preparation prior to injection. Measurement of Pn B0 and Other Species The reversed phase HPLC assay is used to measure Pn B0/Pn C0 and the other species, including Pn E0 and Pn B5. The reversed phase assay uses a gradient HPLC method with an YMC J'Sphere column (JM08S04-2546WT), particle size of 4 mum and pore size of 80 . The column was 250×4.6 mm i.d. and maintained at 30 C. The two mobile phases used were 0.1% phosphoric acid (A) and acetonitrile (B). The elution gradient started at 60% A and 40% B and ramped to 1% A and 99% B over 45 minutes at 1.5 mL/min, with UV detection at 220 nm. Prior to analysis, samples were blown dry under nitrogen and re-dissolved in methanol to the original concentration. Results A typical chromatogram obtained using the proline-modified mobile phase on bare silica gel is shown in FIG. 6. The Pn B0 elutes as a large rich cut as indicated in the figure, with excellent resolution from Pn E0 and Pn B5, which elute in the preceding peak. A chromatogram obtained from a run on the Amide-80 column is shown in FIG. 7. No proline or other modifier was employed in either the mobile phase or feed solvent for this run. A slightly higher level of methanol is used in the feed solvent mixture than for the control case. The retention of Pn B0 on this solid phase was similar to that achieved for the control run with the proline-modified mobile phase (shown in FIG. 6). In fact, the elution profile appears very similar to the control system, except that the main Pn B0 peak is broader. Many fractions were collected from 6 to 14 column volumes (cv) and the fractions were analyzed by both normal and reversed phase HPLC. This analysis confirmed that analogues such as Pn E0 and Pn B5 are well resolved from Pn B0; these analogues were contained in fractions representing 6 to 8.5 cv in FIG. 7. Results of the normal phase analysis indicated that most of Pn C0 was resolved into the fractions representing 13 to 14 cv in FIG. 7. Therefore, the fractions representing 8.5 to 13 cv, shown in FIG. 7, could be combined to give a pure rich cut with yield >90%.
> 90% Purification / work up; A column was prepared containing the N-L-prolyl-3-aminopropyl silica stationary phase; methods for preparing this stationary phase were presented in Examples 5 and 6. The column utilized was 250 mm long×4.6 mm id, and contained the proline-amide moiety bonded to spherical silica from ES Industries which had 5 mum particle size and 60 pore size. The experiment was otherwise identical to that described in Example 8, and the results may also be evaluated against the control in that example as illustrated in FIG. 6. The chromatogram obtained from the run on the N-L-prolyl-3-aminopropyl silica bonded phase is shown in FIG. 8. As illustrated, despite the increased levels of methanol in the feed and the exclusion of proline from the system, the retention of Pn B0 on this phase was similar to that achieved on bare silica using the proline-modified mobile phase (shown in FIG. 6). However, there are some key differences. First, the large solvent front peak normally observed in control system appears diminished. Another difference is that impurities that elute at the leading edge of the main Pn B0 peak appear to be well separated from each other. Finally, there is more tailing of the Pn B0 peak (compared to FIG. 6). Many fractions were collected from 10 to 21 cv and the fractions were analyzed by both normal and reversed phase HPLC. The analytical results indicated the key early eluting impurities such as Pn B5 and Pn E0 were clearly resolved from Pn B0. These impurities are mostly contained in the fraction which represented the 10-13 cv range in FIG. 8. Results of the normal phase analysis indicate most of the Pn C0 was resolved into the fraction that represented the 13 to 14 cv range in FIG. 8. Therefore, 13 to 19 cv (shown in FIG. 8) could be combined to give a pure rich cut with yield >90%.
Purification / work up; Analytical scale HPLC columns, 250 mm long×4.6 mm id, were used to compare the retention and selectivity characteristics obtained with different stationary phases when using an analytical loading of Pneumocandin B0 and its analogues. The different stationary phases included: (1) regular silica, and (2) aminopropyl silica (obtained from Eka Chemicals (Bohus, Sweden)), and (3) Amide-80 (an amide moiety bonded to silica, obtained from Tosoh Biosep LLC. (Japan)). All these packings had a 10 mum particle size and 120 pore diameter. The regular silica was run as a simple liquid chromatography system, and using a mobile phase modified with L-proline, resulting in saturation of the silica with proline. See J. Nti-Gyabaah, et al., ?Large-scale purification of pneumocandin B0, a precursor for CANCIDAS?, PREP-2003, 16th International Symposium, Exhibit and Workshops on Preparative/Process Chromatography, San Francisco, Calif., Wednesday, Jul. 2, 2003 or U.S. Provisional Application No. 60/422,356 filed Oct. 30, 2002. The ternary mobile phase and the feed diluent (84/9/7 v/v/v ethyl acetate, methanol and water) were made using HPLC grade solvents from Fisher Scientific (Pittsburg, Pa., USA). L-proline used for the proline elution silica run was obtained from Ajinomoto (Japan). The L-proline was dissolved in the ternary mobile phase at 0.12 g/L. The feed was prepared by blending pure Pn B0 (crude Pn B0 that had been purified by the standard silica gel method) with aliquots of solutions containing Pn B5, Pn C0 and Pn E0, so that these analogs were each present at roughly 10% the concentration of Pn B0, which was present at roughly 1 g/L. The Pn C0-enriched solution was obtained by selecting tailcut fractions from an injection of crude Pn B0 on silica gel using the standard silica gel method. The Pn B5- and Pn E0-enriched solutions were obtained by selecting forecut fractions from an injection of Pn B0 on silica gel using the proline elution method, and then further purifying those cuts by a reversed-phase method similar to that employed for analytical analysis of Pn B0 (described later in this example) but with higher feed loading. An Agilent HP-1100 HPLC system (Waldbronn, Germany) with diode array detector was used for the HPLC runs, as well as for fraction analysis; a wavelength of 278 nm was used for detection. For each injection, 10 muL of the 1 g/L feed solution was injected. The mobile phase flow rate was 1.1 mL/min. For the run using the proline-modified mobile phase and regular silica, L-proline was dissolved in the mobile phase at 0.12 g/L and 480 mL of the solution was then pumped through the silica column (to in situ coat the silica with proline). The L-proline containing solution was used as eluent for that run. Chromatograms obtained from the runs are shown in FIGS. 1, 2, 3, and 4. For each run, the peaks were identified by collecting fractions and analyzing them by normal and reversed phase HPLC using methods described in U.S. Provisional Application No. 60/422,356 filed Oct. 30, 2002 (incorporated by reference) or J. Nti-Gyabaah, et al., ?Large-scale purification of pneumocandin B0, a precursor for CANCIDAS?, PREP-2003, 16th International Symposium, Exhibit and Workshops on Preparative/Process Chromatography, San Francisco, Calif., Wednesday, Jul. 2, 2003. The retention times of pneumocandins B0, E0, B5 and C0 were then used to calculate the capacity factors, from which the selectivities between Pn B0 and the three analogs were obtained. The results are shown in FIGS. 1-5 and Table 2. TABLE 2 Selectivities between Pneumocandin B0 and analogs Selectivity (Relative to Pn B0) Pn E0 Pn B5 Pn C0 FIGS. Bare silica 1.03 1.05 1.27 1 ?Prolinated? silica* 1.22 1.25 1.26 2 Aminopropyl-silica 1.67 1.66 1.06 3 Amide-80 silica 1.46 1.42 1.25 4 *silica gel chromatography using a proline-modified mobile phase
Purification / work up; A column was prepared containing the N-methylcarbamoyl-3-aminopropyl silica stationary phase; methods for preparing this stationary phase were presented in Examples 3 and 4. The column in this example was 250 mm long×4.6 mm id, and contained the N-methylcarbamoyl-3-aminopropyl silica moiety bonded to spherical silica from ES Industries which had 5 mum particle size and 60 pore size. The experiment was otherwise identical to that described in Example 8, and the results may also be evaluated against the control in that example as illustrated in FIG. 6. A chromatogram obtained from the run on the N-methylcarbamoyl-3-aminopropyl silica bonded phase is illustrated in FIG. 9. Despite the increased methanol in the feed and the exclusion of proline from the system, the retention of Pn B0 on this phase was excellent (compared to FIG. 6). Many fractions were collected from 21 to 40 cv. The fractions were analyzed by normal and reversed phase HPLC. The fraction analysis indicated that the early eluting analogues such as Pn E0 and Pn B5 were well resolved from Pn B0 and contained in the fractions representing 21 to 25 cv, shown in FIG. 9. Results of the normal phase analysis indicated that the resolution of Pn B0 from later eluting analogues such as Pn C0 was comparable to that in the control process. A ring-opened degradate, which was seen at only trace levels if at all in the previous examples, was present at levels of a few percent in the rich cuts of this run. Other than this degradate, the later fractions were very pure.

  • 41
  • [ 110-86-1 ]
  • [ 79271-56-0 ]
  • [ 135575-42-7 ]
  • CF3O3S(1-)*C55H84N9O16(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 80℃; Example 2; Compound of Formula VIII, R1=-(CO)NH2, R2R3H; Pneumocandin B0 (100 mg, 0.094 mmol) was dissolved in pyridine (2 mL), and triethylsilyl triflate (107 muL, 125 mg, 0.47 mmol) was added. The mixture was stirred at 80 C. while the reaction progress was monitored with HPLC. After stirring over night, HPLC indicated 72% conversion to a new compound (compound VI with R1=-(CO)NH2). LC-MS returned the mass m/z 1126.4 for the main product, confirming the pyridine substitution. The mixture was cooled to rt, and 1,2-diaminoethane (2 mL) was added. 15 min later HPLC demonstrated full conversion of the pyridine adduct to another new product for which LC-MS returned the mass m/z 1107.6 which is the expected mass for the title compound. The product was not isolated.
  • 42
  • [ 1493-13-6 ]
  • [ 135575-42-7 ]
  • [ 107-15-3 ]
  • CHF3O3S*C52H86N10O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 1; Compound of Formula VIII, R1=-(CO)NH2, R1R2H; Pneumocandin B0 (2.02 g, 1.90 mmol) and triflic acid (3.0 mL, 5.09 g, 33.9 mmol) were dissolved in pyridine (30 mL) at rt. The mixture was heated to 80 C. and stirred for 12 h in inert atmosphere. After cooling to 0 C., 1,2-diaminoethane (1.00 mL, 0.90 g, 15.0 mmol) was added, and the mixture was stirred over night. The reaction was quenched by adding the reaction mixture to a mixture of water (100 mL) and acetic acid (21 mL, 22.0 g, 0.37 mol), resulting in a solution with pH 5.0. The solution was loaded onto a 10 mm C18 chromatography column eluting with a gradient from 20% acetonitrile/80% water to 25% acetonitrile/75% water. Evaporation of the organic solvent and freeze drying of the rich cuts afforded 534 mg (22% yield) of the title compound as the triflic acid addition salt. Purity, HPLC: 87.8%.1H NMR (600 MHz, CD3OD): delta 7.13 (2H, d, J 8.6 Hz), 6.74 (2H, d, J 8.6 Hz), 5.08 (1H, d, J 4.0 Hz), 5.02 (1H, d, J 3.5 Hz), 4.80 (1H, d, J 1.9 Hz), 4.56-4.52 (m), 4.37 (1H, dt, J 9.4, 3.9 Hz), 4.34 (1H, s), 4.31-4.25 (m), 4.21 (1H, d, J 3.8 Hz), 3.99-3.95 (m), 3.80-3.75 (m), 3.09 (1H, ddd, J 12.9, 6.5, 5.3 Hz), 2.98 (1H, ddd, J 13.0, 6.8, 5.3 Hz), 2.88 (1H, ddd, J 14.9, 6.7, 5.1 Hz), 2.81 (1H, ddd, J 13.4, 6.7, 5.2 Hz), 2.73 (1H, dd, J 15.4, 3.8 Hz), 2.46 (1H, dd, J 15.4, 9.5 Hz), 2.42 (1H, dd, J 13.4, 7.1 Hz), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d, J 6.2 Hz), 1.12-1.03 (m), 0.91 (1H, dt, J 13.5, 7.0 Hz), 0.87 (3H, d, J 7.4 Hz), 0.85 (6H, d, J, 6.6 Hz); 13C NMR (150 MHz, CD3OD): delta 177.0, 175.8, 173.94, 173.92, 173.4, 172.8, 172.6, 169.0, 158.5, 133.1, 129.7, 121.8 (q, 1JC-F316 Hz), 116.2, 77.1, 75.8, 75.1, 71.3, 70.6, 70.3, 69.5, 68.1, 63.9, 62.6, 58.6, 57.2, 56.1, 55.3, 50.9, 47.1, 45.9, 43.1, 40.0, 39.7, 38.5, 38.1, 36.8, 36.4, 34.6, 32.9, 31.2, 31.1, 30.8, 30.6, 30.33, 30.32, 28.0, 27.0, 20.7, 20.2, 19.5, 11.6.
  • 43
  • [ 135575-42-7 ]
  • [ 107-15-3 ]
  • cancidas [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 8; Caspofungin, One-Pot Procedure; Pneumocandin B0 (200 mg, 0.19 mmol) was suspended in THF (3.0 mL), and phenylboronic acid (23 mg, 0.19 mmol) was added. The reaction mixture was stirred at rt over night. Water was removed azeotropically by distillation of THF from the flask, addition of anhydrous THF, and continued distillation to dryness. The mixture was cooled to rt, and anhydrous THF (3.0 mL) was added, followed by BSTFA (15 muL, 0.56 mmol). The mixture was stirred for 1 h at rt and cooled to 0 C. Borane-DMS complex (0.11 ml, 1.13 mmol) was added slowly, and the mixture was stirred for 3 h. Additional borane-DMS complex (0.06 mL, 0.62 mmol) was added, and the reaction mixture was stirred for another 4 h. THF (5.0 mL) was added, and the mixture was stirred over night at 0 C. Pyridine (10 mL) and aqueous hydrochloric acid (2.0 M, 100 muL, 0.2 mmol) were added, and the mixture was concentrated at reduced pressure to about 3 mL. Triflic acid (0.3 mL, 3.38 mmol) was added, and the reaction mixture was stirred at 80 C. for 5 h. The mixture was cooled to 0 C., and 1,2-diaminoethane (0.40 mL, 6.0 mmol) was added. The mixture was then stirred over night at 0 C. HPLC spiking experiments with caspofungin verified the presence of the target compound in the reaction mixture. The purity of caspofungin in the reaction mixture was 18%.
  • 44
  • [ 696-63-9 ]
  • [ 135575-42-7 ]
  • C57H86N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% With trifluoroacetic acid; In acetonitrile; at -15 - -10℃; for 22h; Comparative Example 1: Preparation of phenylthio <strong>[135575-42-7]<strong>[135575-42-7]pneumocandin B</strong>o</strong> compound20.0 g of <strong>[135575-42-7]pneumocandin B</strong>0 was suspended in 600 ml of acetonitrile, and 4.58 g of phenylboronic acid and 5.80 ml of thiophenol were added thereto. The reaction solution was cooled to -15 "C , and 4.98 ml of trifluoromethanesulfonic acid was added thereto. Then, the solution was stirred for 2.5 hours. After completion of the reaction, a solution of 7.66 g of NaOAc-3H20 in 66.6 ml of purified water was added slowly to the reaction solution to precipitate the crystal. Then, the solution was stirred for 2 hours at a temperature of 17 C , and cooled to 0 C . Then, the solution was filtered under reduced pressure, thus obtaining 18.68 g of a phenylthio <strong>[135575-42-7]pneumocandin B</strong>0 compound (yield: 88%).
  • 45
  • [ 62-47-5 ]
  • [ 135575-42-7 ]
  • C54H88N10O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.2% Example 2: Preparation of compound of formula 4 wherein Ri is - CH C(=0)NH(CH2)2NH2 20.0 g of <strong>[135575-42-7]pneumocandin B</strong>0 was suspended in 400 ml of acetonitrile, and the solution was cooled to -5 C . 41.9 ml of trifluoroacetic acid was added thereto, and then stirred for 30 minutes, so that the <strong>[135575-42-7]pneumocandin B</strong>0 was completely dissolved. Then, 7.57 g of N-(2-aminoethyl-2-mercaptoacetamide was added slowly thereto at a temperature between -5 C to 0 C , and the mixture was stirred at 0 "C for 10 hours. After completion of the reaction, 1,300 ml of cold purified water was added to the reaction solution to precipitate the crystal. Then, the solution was stirred at a temperature of 0 C for 1 hour and filtered under reduced pressure, thus separating the crystal from the solution. The obtained crystal was dried in a vacuum, thus obtaining 20.9 g of a white crystalline compound (yield: 94.2%).
  • 46
  • [ 135575-42-7 ]
  • [ 108-98-5 ]
  • C56H84N8O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Comparative Example 1: Preparation of phenylthio <strong>[135575-42-7]<strong>[135575-42-7]pneumocandin B</strong>o</strong> compound20.0 g of <strong>[135575-42-7]pneumocandin B</strong>0 was suspended in 600 ml of acetonitrile, and 4.58 g of phenylboronic acid and 5.80 ml of thiophenol were added thereto. The reaction solution was cooled to -15 "C , and 4.98 ml of trifluoromethanesulfonic acid was added thereto. Then, the solution was stirred for 2.5 hours. After completion of the reaction, a solution of 7.66 g of NaOAc-3H20 in 66.6 ml of purified water was added slowly to the reaction solution to precipitate the crystal. Then, the solution was stirred for 2 hours at a temperature of 17 C , and cooled to 0 C . Then, the solution was filtered under reduced pressure, thus obtaining 18.68 g of a phenylthio <strong>[135575-42-7]pneumocandin B</strong>0 compound (yield: 88%).
  • 47
  • [ 135575-42-7 ]
  • [ 13183-79-4 ]
  • C52H82N12O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.1% Example 3: Preparation of compound of formula 4 wherein Ri is a tetrazole ring or a tetrazole derivative20.0 g of <strong>[135575-42-7]pneumocandin B</strong>0 was suspended in 400 ml of acetonitrile, and the solution was cooled to -5 C . 41.9 ml of trifluoroacetic acid was added thereto, and then stirred for 30 minutes, so that the <strong>[135575-42-7]pneumocandin B</strong>0 was completely dissolved. Then, 6.55 g of 1 -methyl- lH-tetrazole-5-thiol was added slowly thereto at a temperature between -5 C to 0 C , and the mixture was stirred at 0 C for 8 hours. After completion of the reaction, 1,300 ml of cold purified water was added to the reaction solution to precipitate the crystal. Then, the solution was stirred at a temperature of 0 C for 1 hour and filtered under reduced pressure, thus separating the crystal from the solution. The separated crystal was dried in a vacuum, thus obtaining 20.6 g of a white yellow crystalline compound (yield: 94.1%).
  • 49
  • [ 135575-42-7 ]
  • C53H86N8O17S [ No CAS ]
  • 50
  • [ 135575-42-7 ]
  • C54H90N10O16S [ No CAS ]
  • 51
  • [ 135575-42-7 ]
  • C52H84N12O15S [ No CAS ]
  • 52
  • [ 135575-42-7 ]
  • [ 2365-48-2 ]
  • C53H84N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.2% Example 1: Preparation of compound of formula 4 wherein Ri is -CH2C(=0)OCH3 20.0 g of <strong>[135575-42-7]pneumocandin B</strong>0 was suspended in 400 ml of acetonitrile, and the solution was cooled to -5 C . 41.9 ml of trifluoroacetic acid was added thereto, and then stirred for 30 minutes, so that the <strong>[135575-42-7]pneumocandin B</strong>0 was completely dissolved. Then, 5.98 g of methyl-2-mercaptoacetate was added slowly thereto at a temperature between -5 C to 0 C , and the mixture was stirred at 0 C for 6 hours. After completion of the reaction, 1,300 ml of cold purified water was added to the reaction solution to precipitate the crystal. Then, the solution was stirred at a temperature of 0 C for 1 hour and filtered under reduced pressure, thus separating the crystal from the solution. The obtained crystal was dried in a vacuum, thus obtaining 20.4 g of a light-yellow crystalline compound (yield: 94.2%).
  • 53
  • [ 65678-65-1 ]
  • [ 135575-42-7 ]
  • C58H86N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and phenyl mercaptoacetate (431 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product 106. [0067] MS: 1215.48 (M+H+).
  • 54
  • [ 886047-44-5 ]
  • [ 135575-42-7 ]
  • C55H87N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N-cyclopropyl mercaptoacetamide (370 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC12. [0084] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.21-3.09 (dd, 1H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.87-1.85 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 2H), 0.87 (d, 3H), 0.85 (d, 6H) 0.680.50 (m, 4H); [0085] MS: 1178.46 (M+H+).
  • 55
  • [ 1403982-65-9 ]
  • [ 135575-42-7 ]
  • C57H91N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N-cyclopentyl mercaptoacetamide (450 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC13. [0087] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.21-3.09 (dd, 1H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.94-1.90 (m, 4H), 1.87-1.85 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 2H), 0.89-0.85 (m, 15H); [0088] MS: 1206.50 (M+H+).
  • 56
  • [ 58458-67-6 ]
  • [ 135575-42-7 ]
  • C55H89N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N-isopropyl mercaptoacetamide (370 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC14. [0090] MS: 1180.50 (M+H+).
  • 57
  • [ 4822-44-0 ]
  • [ 135575-42-7 ]
  • C58H87N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N-phenyl mercaptoacetamide (370 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC15. [0092] MS: 1214.65 (M+H+).
  • 58
  • [ 135575-42-7 ]
  • [ 100-53-8 ]
  • C57H86N8O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and benzyl mercaptan (350 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC16. [0094] 1H NMR (CD3OD, 400 MHz) delta 7.30-7.27 (d, 2H), 7.24-7.2 (t, 3H), 7.17-7.15 (d, 1H), 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.63 (s, 3H), 3.55-3.51 (dd, 1H), 3.36-3.40 (dd, 1H), 2.88 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0095] MS: 1171.10 (M+H+).
  • 59
  • [ 135575-42-7 ]
  • [ 2365-48-2 ]
  • C53H84N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (PB0, prepared by microbial fermentation) (500 mg), phenyl boronic acid (172 mg), and methyl mercaptoacetate (299 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC1. [0055] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.29 (d, 1H), 5.1 (d, 1H), 4.99 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.63 (s, 3H), 3.55-3.51 (dd, 1H), 3.36-3.40 (dd, 1H), 2.88 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0056] MS: 1153.26 (M+H+).
  • 60
  • [ 35331-24-9 ]
  • [ 135575-42-7 ]
  • C54H87N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N, N-dimethyl mercaptoacetamide (336 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC8. [0072] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.01 (s, 1H), 2.88 (s, 1H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0073] MS: 1166.52 (M+H+).
  • 61
  • [ 20939-05-3 ]
  • [ 135575-42-7 ]
  • C54H87N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N, N-dimethyl mercaptoacetamide (259 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC9. [0075] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 2.88 (dd, 2H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0076] MS: 1166.52 (M+H+).
  • 62
  • [ 10047-28-6 ]
  • [ 135575-42-7 ]
  • C56H90N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and butyl mercaptoacetate (417 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC3. [0061] MS: 1195.48 (M+H+).
  • 63
  • [ 135575-42-7 ]
  • [ 68-11-1 ]
  • C52H82N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and mercaptoacetic acid (259 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC2. [0058] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 2.88 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0059] MS: 1139.18 (M+H+)
  • 64
  • [ 758-08-7 ]
  • [ 135575-42-7 ]
  • C52H83N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and mercaptoacetamide (259 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC7. [0069] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 2.88 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 1H), 0.87 (d, 3H), 0.85 (d, 6H). [0070] MS: 1138.45 (M+H+).
  • 65
  • [ 135575-42-7 ]
  • N-(n-butyl)-2-mercaptoacetamide [ No CAS ]
  • C56H91N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N, N-dimethyl mercaptoacetamide (414 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC10. [0078] 1H NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 2.94-2.91 (t, 2H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.97-1.90 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 2H), 0.87 (d, 6H), 0.85 (d, 6H). [0079] MS: 1194.53 (M+H+).
  • 66
  • 1-mercaptoacetylpyrrolidine [ No CAS ]
  • [ 135575-42-7 ]
  • C56H89N9O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and N-pyrrolyl mercaptoacetamide (410 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC11. [0081] 1H-NMR (CD3OD, 400 MHz) delta 7.09 (d, 2H), 6.70 (d, 2H), 5.24 (d, 1H), 5.04 (d, 1H), 4.90 (d, 1H), 4.56-4.47 (m), 4.39-4.35 (m, 2H), 4.31-4.25 (m), 4.23-4.21 (m, 3H), 3.99-3.95 (m), 3.80-3.75 (m), 3.18-3.14 (m, 4H), 2.68 (dd, 1H), 2.46 (dd, 1H), 2.42 (dd, 1H), 2.26-2.18 (m), 2.10-2.03 (m), 1.94-1.90 (m, 4H), 1.87-1.85 (m), 1.63-1.52 (m), 1.51-1.46 (m), 1.45-1.39 (m), 1.38-1.20 (m), 1.14 (d), 1.12-1.03 (m), 0.91 (dt, 2H), 0.87 (d, 3H), 0.85 (d, 6H); [0082] MS: 1192.56 (M+H+).
  • 67
  • [ 135575-42-7 ]
  • [ 162808-60-8 ]
  • 69
  • [ 20291-99-0 ]
  • [ 135575-42-7 ]
  • C56H90N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and tert-butyl mercaptoacetate (417 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product IC4. [0063] MS: 1195.48 (M+H+).
  • 70
  • [ 103604-39-3 ]
  • [ 135575-42-7 ]
  • C57H90N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -15℃;Inert atmosphere; A suspension of compound IIC (500 mg), phenyl boronic acid (172 mg), and cyclopentyl mercaptoacetate (431 mg) in anhydrous acetonitrile (30 mL) was added dropwise to a solution of trifluoromethylsulfonic acid (282 mg) in acetonitrile at -15 C. under nitrogen atmosphere. The reaction mixture was stirred at the same temperature for 4-6 hours to complete the reaction. After addition of sodium acetate aqueous solution and stirring for 1-2 hours, water (90 mL) was added to the reaction mixture followed by stirring for another one hour. Then the reaction mixture was filtered and the filter cake was collected and dried under vacuum to give product 105. [0065] MS: 1207.49 (M+H+).
  • 71
  • [ 40248-84-8 ]
  • [ 135575-42-7 ]
  • C56H84N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With trifluoroacetic acid; phenylboronic acid; In acetonitrile; at -50 - -45℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, acetonitrile (100 ml), the compound of formula (2) (5.0 g), phenylboronic acid (0.90 g) and 3-mercaptophenol (1.80 g) were uniformly stirred and the temperature was raised to -50 to -45C And trifluoroacetic acid (1.05 ml) was added dropwise. After the dropwise addition, the mixture was reacted at -50 to -45C for about 2.5 hours. After confirming the completion of the reaction by TLC monitoring, the reaction was stopped and an aqueous solution of NaOAc (1.15 g NaOAc dissolved in 25 ml of water) was added slowly, and the temperature was raised to 20 C and stirred for 2 hours. A large amount of solid was precipitated, the temperature was lowered to 0 C or lower, and the filtrate was subjected to third washing with 60 ml of acetonitrile / water = 9: 1 (V / V), followed by vacuum drying for 5 hours, 3b (4.65 g, yield 93%).
0.72 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -50 - -45℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, acetonitrile (20 ml),The compound of formula 2 (1.0 g), (0.12 g) and 3-mercaptophenol (0.40 g) were uniformly stirred and the temperature was lowered to -50 to -45 C, and trifluoroacetic acid (0.21 g) was added dropwise. After dropwise addition, To -45 & lt; 0 & gt; C for 2.5 hours. After confirming the end of the reaction by TLC monitoring and stopping the reactionAfter slowly adding an aqueous NaOAc solution (0.23 g NaOAc dissolved in 5 ml of water), the temperature was raised to 20 C and stirred for 2 hours. A large amount of solid precipitated, the temperature was lowered to below 0 C and filtered, and the filter cake was washed with acetonitrile /Water = 9: 1 (v / v) 12.5 ml, And dried under vacuum for 5 hours to obtain 0.72 g of a compound of formula (3b) as a sample.
  • 72
  • [ 1121-24-0 ]
  • [ 135575-42-7 ]
  • C56H84N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.75 g With methanesulfonic acid; phenylboronic acid; In acetonitrile; at 35 - 45℃; for 1.5h;Inert atmosphere; Under nitrogen gas protection,Acetonitrile (20 ml), The compound of formula 2 (1.0 g), Phenyl boronic acid (0.14 g) and 2-mercaptophenol(0.35 g) were uniformly stirred, The temperature was raised to 35 to 45 DEG C,Methanesulfonic acid (0.27 ml) was slowly added dropwise,After the fall,And the reaction was carried out at 35 to 40 DEG C for about 1.5 hours. After the end of the reaction was confirmed by TLC monitoring,Quenched and an aqueous NaOAc solution (0.23 g NaOAc in 5 ml water) was slowly added dropwise, and after the dropwise addition was complete,The temperature was raised to 20 C and stirred for 2 hours. After a large amount of solid was precipitated, the temperature was lowered to below 0 C and filteredThen, the filter cake was subjected to third washing with 12.5 ml of acetonitrile / water = 9: 1 (v / v) and vacuum drying for 4 hours to obtain a sample3c (0.75 g).
0.96 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at 35 - 45℃; for 2.5h;Inert atmosphere; acetonitre (200 ml), the compound of formula (2) (1.0 g), phenylboronic acid (0.12 g) and 2-mercaptophenol (0.35 g) were uniformly stirred under the nitrogen gas protection, Trifluoromethanesulfonic acid (0.35 ml) was slowly added dropwise. After the dropwise addition, the mixture was reacted at 35 to 45 C for about 2.5 hours. After confirming the completion of the reaction by TLC monitoring, the reaction was coupled and NaOAc aqueous solution (0.23 g NaOAc dissolved in 5 ml water) was slowly added dropwise. After dropwise addition, the temperature was raised to 20 C and stirred for 2 hours. After the precipitation of a large amount of solid, the temperature was lowered to 0 C or less, and the filtrate cake was subjected to third washing with 12.5 ml of acetonitrile / water = 9: 1 (v / v) and vacuum drying for 4 hours, (0.96 g) was obtained
  • 73
  • [ 32281-01-9 ]
  • [ 135575-42-7 ]
  • C57H86N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With methanesulfonic acid; phenylboronic acid; In acetonitrile; at -15 - 40℃; for 2.5h;Inert atmosphere; After uniformly stirring acetonitrile (200 ml), the compound of Formula 2 (5.0 g), phenylboronic acid (1.50 g) and 4-hydroxy-3-methylthiophenol (2.05 g) under nitrogen gas protection, Methanesulfonic acid (1.36 g) was slowly added dropwise at a temperature lower than -15C and after dropwise addition, the temperature was raised to 35 to 40 C and reacted for 2.5 hours. After confirming the completion of the reaction by TLC monitoring, the reaction was combined, and an aqueous solution of NaOAc (1.20 g NaOAc dissolved in 20 ml water) was slowly added dropwise. After dropwise addition, the temperature was raised to 20 C and stirred for 2 hours. After the precipitation of a large amount of solid, the temperature was lowered to 0 C or less, and the filtrate cake was subjected to third washing with 50 ml of acetonitrile / water = 9: 1 (V / V) and vacuum drying for 5 hours, 3c (4.60 g, yield 92%).
0.75 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -50 - -45℃; for 1h;Inert atmosphere; Under nitrogen gas protection, acetonitrile (30 ml),The compound of formula 2 (1.0 g),Phenylboronic acid (0.23 g) and 4-hydroxy-3-methylthiophenol (0.41 g) were uniformly stirred,Lowering the temperature to -50 to -45 [deg.] C,Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise,After the fall,The temperature was lowered to -50 to -45 and the reaction was carried out for about 1 hour.After confirming the completion of the reaction by TLC monitoring,The reaction was quenched and aqueous NaOAc solution (0.23 g NaOAc in 3.5 ml water) was slowly added dropwise,After the fall,The temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid has been depositedAfter lowering the temperature to below 0 C and filtering, the filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v)And vacuum drying was conducted for a period of time to obtain a compound (0.75 g) as a samp
  • 74
  • [ 27320-22-5 ]
  • [ 135575-42-7 ]
  • C56H84N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -50 - 45℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, acetonitrile (30ml), the compound of formula 2 (1.0g), phenyl boronic acid (0.23g) and 3,4-dihydroxy-thiophenol (0.42g),lowering the temperature -50 to -45 C trifluoromethanesulfonic acid(0.25ml) was slowly added dropwise with methane sulfonic acid after the addition was ended, the temperature -50 to -45C was reacted down to about 2.5 hours. After confirming the reaction by TLC monitoring ends, (0.23g NaOAc dissolved in 3.5ml of water) the binding reaction and NaOAc solution was slowly added dropwise, after the addition was finished, which was stirred for 2 hours, the temperature was raised to 20 . After large amount of solid had precipitated was filtered again lowering the temperature to below 0 , filtered acetonitrile / water cake = 9: 1 (V / V) to the third washing, and vacuum drying for five hours, to 12.5ml samples of to give the compound of formula 3e (0.82g, 87% yield).
0.7 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -20 - -15℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, acetonitrile (30 ml), the compound of formula (2) (1.0 g), phenylboronic acid (0.23 g) and 3,4-After the phenol (0.42 g) was uniformly stirred, the temperature was lowered to -20 to -15 C, and trifluoromethanesulfonic acid (0.25 ml)After the dropping, the temperature was lowered to -20 to -15 C and the reaction was continued for about 2.5 hours. With TLC monitoringAfter confirming the end of the reaction, the reaction was quenched and slowly added an aqueous NaOAc solution (0.23 g NaOAc in 3.5 ml water)After dropwise addition, the temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid precipitates,After the temperature was lowered to below 0 C and filtered, the filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v)(0.70 g) as a sample.
  • 75
  • 3-bromo-4-hydroxythiophenol [ No CAS ]
  • [ 135575-42-7 ]
  • C56H83BrN8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.97 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -10 - -5℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection,Acetonitrile (30 ml),The compound of formula 2 (1.0 g),Phenylboronic acid (0.23 g) and 3-bromo-4-hydroxythiophenol (0.59 g) were uniformly stirred,Lowering the temperature to -10 to -5 [deg.] C,Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise,After the fall,The temperature was lowered to -10 to -5 DEG C and the reaction was carried out for 2.5 hours.With TLC monitoringAfter confirming the end of the reaction, the reaction was quenched and aqueous NaOAc solution (0.23 g NaOAc in 3.5 ml water) was added slowlyAfter dropwise addition, the temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid has been depositedAfter lowering the temperature to below 0 C and filtering, the filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v)And dried under vacuum for a period of time to obtain 0.97 g of a compound represented by the general formula (3f)
  • 76
  • 4-hydroxy-2-methoxythiophenol [ No CAS ]
  • [ 135575-42-7 ]
  • C57H86N8O18S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -20 - -15℃; for 2.5h;Inert atmosphere; The compound of formula (2)Under nitrogen gas protection,Acetonitrile (30 ml),The compound of formula 2 (1.0 g),Phenylboronic acid (0.23 g) and 4-hydroxy-2-methoxythiophenol (0.45 g) were uniformly stirred,Lower the temperature to -20 to -15 & lt; RTI ID = 0.0 & gt;Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise,After the fall,The temperature was lowered to -20 to -15 DEG C and the reaction was carried out for about 2.5 hours.TLC monitoring, The reaction was quenched and a solution of NaOAc (0.23 g NaOAc in 3.5 ml water) was addedAfter dropwise addition, the temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid has been precipitatedAfter lowering the temperature to below 0 C and filtering, the filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v)And dried under vacuum to obtain 0.98 g of a compound of the formula (3g) as a sample
  • 77
  • 4-hydroxy-2-nitrothiophenol [ No CAS ]
  • [ 135575-42-7 ]
  • C56H83N9O19S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.94 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at 0 - 5℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, Acetonitrile (30 ml),The compound of formula 2 (1.0 g),Phenylboronic acid (0.23 g) and 4-hydroxy-2-nitrothiophenol (0.49 g) were uniformly stirred, the temperature was lowered to 0 to 5 C,Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise, After the fall,The temperature was lowered to 0 to 5 and the reaction was carried out for about 2.5 hours. Reaction with TLC monitoringAfter confirming the end, the reaction is quenched and aqueous NaOAc solution (0.23 g NaOAc in 3.5 ml water) is slowly addedAfter dropwise addition, the temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid precipitates,After the temperature was lowered to below 0 C and filtered, the filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v)And vacuum dried to obtain 0.94 g of a compound of the formula (3h) as a sample.
  • 78
  • [ 38778-05-1 ]
  • [ 135575-42-7 ]
  • C62H88N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.05 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at 35 - 40℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, Acetonitrile (30 ml),The compound of formula 2 (1.0 g), Phenylboronic acid (0.23 g) and 4-phenoxythiophenol (0.58 g) were uniformly stirred, the temperature was lowered to 35 to 40 C or lower,Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise, After the fall, The temperature was lowered to 35 to 40 and reacted for about 2.5 hours.The reaction with TLC monitoringAfter the end is confirmed, the reaction is quenched and a solution of NaOAc in water (0.23 g NaOAc in 3.5 ml water) is slowly added dropwiseAfter dropwise addition, the temperature was raised to 20 C and stirred for 2 hours. After a large amount of solid was precipitated,The filtrate cake was subjected to third washing with 12.5 ml of acetonitrile / water = 9: 1 (v / v) for 5 hoursAnd dried under vacuum to obtain a compound (3H) as a sample (1.05 g).
  • 79
  • p-methylphenoxythiophenol [ No CAS ]
  • [ 135575-42-7 ]
  • C63H90N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.05 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at 25 - 30℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection,Acetonitrile (30 ml),The compound (2) (1.0 g), phenylboronic acid (0.23 g) and p-methylphenoxythiophenol (0.62 g) were uniformly stirred,Lowering the temperature to 25 to 30 DEG C, Trifluoromethanesulfonic acid (0.25 ml) was slowly added dropwise,After the fall,The reaction was carried out at 25 to 30 DEG C for about 2.5 hours.TLC monitoring confirms the end of the reaction, The reaction was quenched and aqueous NaOAc solution (0.23 g NaOAc in 3.5 ml water) was slowly added dropwise,After dropwise addition, the temperature was raised to 20 DEG C and stirred for 2 hours. After a large amount of solid is precipitated, the temperature is lowered to 0 deg., The filter cake was washed three times with 12.5 ml of acetonitrile / water = 9: 1 (v / v) and vacuum dried for 5 hoursTo obtain a compound of the formula (3j) (1.05 g) as a sample.
  • 80
  • [ 637-89-8 ]
  • [ 135575-42-7 ]
  • C56H84N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.93 g With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -20 - -15℃; for 2.5h;Inert atmosphere; Under nitrogen gas protection, Acetonitrile (30 ml),The compound of formula 2 (1.0 g),Phenylboronic acid (0.12 g) and 4-mercaptophenol (0.361 g) were uniformly stirred and the temperature was lowered to -20 to -15 C, Trifluoromethanesulfonic acid (0.25 ml) was added dropwise, And the reaction was carried out at -20 to -15 DEG C for about 2.5 hours. The reaction was completely confirmed by TLC and the reaction was quenched.An aqueous NaOAc solution (0.23 g NaOAc in 5 ml water) was slowly added,The temperature was raised to 20 C and reacted for 2 hours. When a large amount of solid precipitates,The temperature was again lowered to below 0 C,Filtered, The filter cake was washed with acetonitrile / water = 9:1 (V / V), and after the third washing,Followed by vacuum drying for 5 hours to obtain a compound (0.93 g) of the formula (3a).
  • 81
  • [ 135575-42-7 ]
  • C56H86N8O16S [ No CAS ]
  • 82
  • [ 135575-42-7 ]
  • C57H88N8O16S [ No CAS ]
  • 83
  • [ 135575-42-7 ]
  • C56H86N8O16S [ No CAS ]
  • 84
  • [ 637-89-8 ]
  • [ 135575-42-7 ]
  • C56H84N8O17S [ No CAS ]
YieldReaction ConditionsOperation in experiment
95.2% With trifluorormethanesulfonic acid; phenylboronic acid; In acetonitrile; at -20 - -15℃; for 2.5h;Inert atmosphere; Under a nitrogen gas protection, acetonitrile (150 ml), the compound of the formula (2) (5.0 g), phenylboronic acid (0.60 g) and 4-mercaptophenol (1.81 g) were uniformly stirred-20 to -15C, trifluoromethanesulfonic acid (1.25 ml, 14.13 mmol) was added dropwise, and the mixture was reacted at -20 to -15C for about 2.5 hours. The reaction was completely confirmed by TLC and the reaction was bound. NaOAc aqueous solution (1.15 g NaOAc dissolved in 25 ml water) was added slowly, the temperature was raised to 20 C, and the reaction was allowed to proceed for 2 hours. When a large amount of solid precipitates, the temperature is lowered again to 0 C or lower, and the filter cake is washed with 60 ml of acetonitrile / water = 9: 1 (V / V) To obtain the compound of Formula 3a (4.76 g, yield 95.2%). (Note: all the yields are in mass yield).
  • 85
  • [ 637-89-8 ]
  • [ 135575-42-7 ]
  • C56H86N8O16S [ No CAS ]
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