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Chemical Structure| 91183-71-0 Chemical Structure| 91183-71-0
Chemical Structure| 91183-71-0

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Synonyms: H-Met-OtBu.HCl

4.5 *For Research Use Only !

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Product Details of H-Met-OtBu·HCl

CAS No. :91183-71-0
Formula : C9H20ClNO2S
M.W : 241.78
SMILES Code : O=C(OC(C)(C)C)[C@@H](N)CCSC.[H]Cl
Synonyms :
H-Met-OtBu.HCl
MDL No. :MFCD00038896
InChI Key :KZJQROCWHZGZBJ-FJXQXJEOSA-N
Pubchem ID :13141795

Safety of H-Met-OtBu·HCl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of H-Met-OtBu·HCl

* 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 [ 91183-71-0 ]

[ 91183-71-0 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 91183-71-0 ]
  • [ 530-62-1 ]
  • [ 106015-56-9 ]
  • 3
  • [ 83896-44-0 ]
  • [ 91183-71-0 ]
  • glycyrrhizic acid L-methionine tert-butyl ester triamide [ No CAS ]
  • 4
  • [ 91183-71-0 ]
  • [ 166169-36-4 ]
  • [ 166169-37-5 ]
  • 5
  • [ 50-00-0 ]
  • [ 91183-71-0 ]
  • 2-methyleneamino-4-methylsulfanyl-butyric acid <i>tert</i>-butyl ester [ No CAS ]
  • 6
  • [ 138-41-0 ]
  • [ 91183-71-0 ]
  • 4-methylsulfanyl-2-(4-sulfamoyl-benzoylamino)-butyric acid <i>tert</i>-butyl ester [ No CAS ]
  • 7
  • [ 1205-30-7 ]
  • [ 91183-71-0 ]
  • 2-(4-chloro-3-sulfamoyl-benzoylamino)-4-methylsulfanyl-butyric acid <i>tert</i>-butyl ester [ No CAS ]
  • 8
  • [ 91183-71-0 ]
  • [ 501-52-0 ]
  • N-methyl-L-phenylalanine allyl ester hydrochloride [ No CAS ]
  • N,O-dimethyl-L-tyrosine allyl ester hydrochloride [ No CAS ]
  • Fmoc-D-Tyr(O-Wang resin)-OAll [ No CAS ]
  • N-3-phenylpropionyl-D-tyrosyl-N,O-dimethyl-L-tyrosyl-N-methyl-L-phenylalanyl-L-methionine methyl ester [ No CAS ]
  • 9
  • [ 91183-71-0 ]
  • [ 4457-32-3 ]
  • N-methyl-L-phenylalanine allyl ester hydrochloride [ No CAS ]
  • N,O-dimethyl-L-tyrosine allyl ester hydrochloride [ No CAS ]
  • Fmoc-D-Tyr(O-Wang resin)-OAll [ No CAS ]
  • (S)-2-[(S)-2-[(R)-3-(4-Hydroxy-phenyl)-2-(4-nitro-benzyloxycarbonylamino)-propionyl]-methyl-amino}-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-3-phenyl-propionic acid [ No CAS ]
  • N-4-nitrobenzyloxycarbonyl-D-tyrosyl-N,O-dimethyl-L-tyrosyl-N-methyl-L-phenylalanyl-L-methionine [ No CAS ]
  • N-4-nitrobenzyloxycarbonyl-D-tyrosyl-N,O-dimethyl-L-tyrosyl-N-methyl-L-phenylalanyl-L-methionine sulfoxide [ No CAS ]
  • 10
  • [ 852325-32-7 ]
  • [ 91183-71-0 ]
  • [ 852325-33-8 ]
  • 11
  • [ 91183-71-0 ]
  • [ 150841-01-3 ]
  • 3-oxo-17β-(O-tert-butyl-L-methionin-N-yl)carbonyl-28-norlup-20(29)-ene [ No CAS ]
  • 12
  • [ 91183-71-0 ]
  • [ 136789-10-1 ]
  • 13
  • [ 91183-71-0 ]
  • 2-[3-(1-tert-Butoxycarbonyl-3-methylsulfanyl-propyl)-1-(4-[2-(dimethylamino-methyleneamino)-5-methyl-4-oxo-3,4,5,6,7,8-hexahydro-pteridin-6-ylmethyl]-amino}-benzoyl)-ureido]-pentanedioic acid dibutyl ester [ No CAS ]
  • 14
  • [ 91183-71-0 ]
  • [ 106044-01-3 ]
  • 15
  • [ 223761-08-8 ]
  • [ 91183-71-0 ]
  • tert-butyl (2S)-2-{2-(4-fluorophenyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxymethyl]pyrid-3-oylamino}-4-methylsulfanylbutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; 2-(4-Fluorophenyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxymethyl]pyrid-3-carboxylic acid (0.39 g) and <strong>[91183-71-0]L-methionine-tert-butyl-ester.HCl</strong> (0.42 g) were dissolved in DMF (50 ml) then DMAP (0.63 g), EDC (0.25 g) and HOBT (0.12 g) were added under an inert atmosphere at ambient temperature. After 16 hours the solution was evaporated under reduced pressure, the residue obtained was diluted with 1M citric acid (10 ml) and extracted with 2% methanol/dichloromethane (1×100 ml, 1×60 ml). The combined extracts were dried, filtered and concentrated under reduced pressure to give a yellow oil. Purification by flash column chromatography eluting with methanol/ethyl acetate (9:1) gave tert-butyl (2S)-2-{2-(4-fluorophenyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxymethyl]pyrid-3-oylamino}-4-methylsulfanylbutyrate as a colourless foam (0.34 g). 1H NMR (CDCl3) delta 1.43 (9H, s), 1.82-1.95 (2H, m), 2.04 (3H, s), 2.20-2.29 (2H, m), 2.88-2.99 (1H, m), 3.02-3.14 (1H, m), 3.20 (2H, s), 4.41-4.49 (1H, m), 4.55-4.66 (3H, m), 6.48 (1H, dd), 6.76 (1H, s), 7.00-7.15 (4H, m), 7.23-7.31 (4H, m), 7.58-7.66 (2H, m), 7.90(1H, dd). Anal. Calculated allowing for 0.5 H2O: C, 63.2; H, 6.1; N, 8.7; Found: C, 63.0; H, 5.8; N, 8.7; MS (MH+) 637.4.
  • 16
  • [ 223761-14-6 ]
  • [ 91183-71-0 ]
  • tert-butyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20℃; for 16h; 3-(4-Fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylic acid (0.61 g) and <strong>[91183-71-0]L-methionine-tert-butyl-ester.HCl</strong> (0.64 g) were dissolved in dichloromethane (50 ml) then DMAP (0.96 g) and EDC (0.38 g) were added under an inert atmosphere at ambient temperature. After stirring for 16 hours the solution was washed with 1M citric acid (60 ml) and the organic layer dried and concentrated under reduced pressure. Purification on a silica flash column eluting with ethyl acetate gave tert-butyl (2S)-2-{3-(4-fluorophenethyl)-6-[1-4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyrid-2-oylamino}-4-methylsulfanylbutyrate as a colourless foam (0.27 g). 1H NMR (CDCl3) delta: 1.54 (9H, d), 1.75-1.98 (2H, m), 2.05 (3H, s), 2.12-2.29 (1H, m), 2.33-2.63 (1H, m), 2.76-2.88 (2H, m), 3.06-3.30 (4H, m), 3.42 (3H, s), 4.63-4.73 (1H, m), 6.05-6.21 (1H, m), 6.76-7.03 (5H, m), 7.06-7.16 (2H, m), 7.26-7.42 (4H, m), 8.06-8.14 (1H, m). Anal. Calculated allowing for 1.5 HCl: C, 59.6; H, 5.9; N, 7.9. Found: C, 59.8; H, 5.9; N, 7.7; MS(MH+) 651.
  • 17
  • [ 223761-21-5 ]
  • [ 91183-71-0 ]
  • [ 223761-22-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; A mixture of 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoic acid (0.74 g, 1.63 mmol), DMAP (1.0 g, 8.2 mmol), L-methionine tert-butyl ester HCl (1.0 g, 4.92 mmol), EDC (0.63 g, 3.27 mmol) and HOBT (0.22 g, 1.63 mmol) in DMF (50 ml) was stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The reaction was evaporated to dryness and washed with aqueous citric acid (1M, 20 ml) and extracted with dichloromethane (20 ml). The extracts were washed with saturated brine and dried and applied directly onto a silica flash column which was eluted with ethyl acetate/methanol (9:1 and 4:1) to give tert-butyl (2S)-2- {2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate. The product was dissolved in ethyl acetate and treated with 1M ethereal HCl (10 ml). The resulting solid was isolated by centrifuging, flirther washing with diethyl ether and finally drying under high vacuum to give tert-butyl (2S)-2-{2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxy]benzoylamino}-4-methylsulfanylbutyrate as a white solid, (0.57 g, 54% Yield). 1H NMR (CDCl3) delta: 1.45-1.53 (9H, s), 1.99-2.10 (1H, m), 2.08 (3H, s), 2.16-2.31 (1H, m), 2.51-2.63 (2H, t), 2.78-2.97 (2H, m), 2.92-3.00 (2H, m), 3.30-3.4 (2H, m), 3.57 (3H, s), 4.66-4.78 (1H, m), 5.68-5.73 (1H, m), 6.47-6.55 (1H, t), 6.77-7.13 (8H, m), 7.40-7.45 (2H, m), 7.80 (1H, d). Anal. Calculated allowing for: 2 HCl 2H2O C, 53.00; H, 6.07; N, 7.49; S, 8.58; Found: C, 53.00; H, 6.20; N, 7.00; S, 8.70; MS (MH+). 439.4.
  • 18
  • [ 223761-25-9 ]
  • [ 91183-71-0 ]
  • [ 223760-23-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; A mixture of 2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid (0.47 g, 1.06 mmol) (from Example 63), DMAP (0.62 g, 5.05 mmol), L-methionine tert-butyl ester HCl (0.62 g, 3.02 mmol), EDC (0.39 g, 2.02 mmol) and HOBT (0.137 g, 1.01 mmol) in DMF (25 ml) was stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The reaction was evaporated to dryness and washed with aqueous citric acid (1M, 10 ml) and extracted with dichloromethane (20 ml). The extracts were washed with saturated brine, dried and filtered. Purification by flash column chromatography eluting with dichloromethanel methanol (95:5, 9:1 and 85:15) gave a gum. This was dissolved in ethyl acetate and treated with 1M ethereal HCl (10 ml). The resulting solid precipitate was isolated by centrifuging, further washing with diethyl ether and drying under high vacuum to give tert-butyl (2S)-2- (2-(4-fluorophenethyl)-5-[1-(thiazol-2-yl)-2-(1 -methylimidazol-5-yl)ethoxymethyl]benzoylamino}-4-methylsulfanylbutyrate as a white solid, (0.366 g, 55%). 1H NMR (CDCl3) delta: 1.51(9H, s), 1.92-2.08 (1H, m), 2.15-2.33 (1H, m), 2.59-2.70 (2H, m), 2.85-2.98 (5H, m), 3.00-3.23 (4H, m), 3.46 (3H, d), 4.34 (1H, d), 4.52 (1H, dd), 4.70-4.83 (1H, m), 4.83-4.90 (1H, m), 6.77 (1H, d), 6.99-7.08 (3H, m), 7.12-7.21 (5H, m), 7.38 (1H, d), 7.80 (1H, d). Anal. Calculated allowing for: 2.75 H2O,1 HCl C, 55.27; H, 6.48; N, 7.58; S, 8.68; Found: C, 55.00; H, 6.70; N, 7.50; S, 9.00; MS (MH+). 653.4.
  • 19
  • [ 223761-27-1 ]
  • [ 91183-71-0 ]
  • [ 223760-25-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; A mixture of 2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid (0.44 g, 1.07 mmol) (from Example 65), DMAP (0.62 g, 5.03 mmol), L-methionine tert-butyl ester HCl (0.62 g, 5.03 mmol), EDC (0.39 g, 2.01 mmol) and HOBT (0.138 g, 1.01 mmol) in DMF (25 ml) was stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The reaction was evaporated to dryness, the residue treated with aqueous citric acid (1M, 10 ml) and then extracted with dichloromethane (20 ml). The extracts were washed with saturated brine, dried and applied directly to a silica flash column eluting with dichloromethane/methanol (95:5, 9:1 and 85:15) to give a gum. This was dissolved in ethyl acetate and treated with ethereal 1M HCl (10 ml). The resulting solid was isolated by centrifuging, further washing with diethyl ether and drying under high vacuum to give tert-butyl (2S)-2-{2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoylamino}-4-methylsulfanylbutyrate as a white solid, (0.373 g, 59%). 1H NMR (DMSO-d6) delta: 1.49 (9H, s), 1.80-2.00 (2H, m), 2.06 (3H, s), 2.20-2.40 (2H, m), 3.13-3.31 (4H, m), 4.22-4.32 (1H, m), 4.70 (2H, q), 5.11 (1H, q), 6.63 (1H, s), 7.20-7.30 (2H, m), 7.30-7.51(7H, m), 7.80 (1H, d), 7.80 (1H, d), 7.89 (1H, d), 8.53 (1H, d). Anal. Calculated allowing for: 1.5 H2O, 1.5 HCl C, 54.40; H, 5.92; N, 7.93; S, 9.08; Found: C, 54.40; H, 6.00; N, 7.80; S, 9.00; MS (MH+). 625.4.
  • 20
  • [ 223761-27-1 ]
  • [ 91183-71-0 ]
  • [ 223760-26-7 ]
YieldReaction ConditionsOperation in experiment
62% With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20℃; for 16h; A mixture of 2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoic acid (0.44 g, 1.07 mmol), DMAP (0.61 g, 5.04 mmol), L-methionine tert-butyl ester HCl (0.71 g, 3.03 mmol), EDC (0.39 g, 2.01 mmol) and HOBT (0.138 g, 1.01 mmol) in DMF (25 ml) was stirred at ambient temperature under a nitrogen atmosphere for 16 hours. The reaction was evaporated to dryness and washed with aqueous citric acid (1M, ml) and extracted with dichloromethane (20 ml). The extracts were washed with saturated brine, dried and filtered. Purification by flash column chromatography eluting with dichloromethane/methanol (95:5, 9:1 and 85:15) gave a gum. This was dissolved in ethyl acetate and treated with ethereal 1M HCl (10 ml). The resulting solid was isolated by centrifuging, further washing with diethyl ether and drying under high vacuum to give tert-butyl (2S)-2-{2-(4-fluorophenyl)-4-[1-(thiazol-2-yl)-2-(1-methylimidazol-5-yl)ethoxymethyl]benzoylamino}-4-methylsulfonylbutyrate as a white solid, (0.406 g, 62%). 1H NMR (DMSO-d6) delta: 1.40 (9H, s),1.82-2.02 (1H, m), 2.02-2.12 (1H, m), 2.73-2.89 (1H, m), 2.93 (3H, s), 2.95-3.10 (2H, m), 3.10-3.25 (2H, m), 3.45 (3H, s), 4.18 4.28 (1H, m),4.63 (2H, q), 5.02 (1H, q0, 6.60 (1H, s), 7.10-7.25 (2H, m),7.25-7.50 (7H, m), 7.71 (1H, d), 7.81 (1H, d), 8.79 (1H, d). Anal. Calculated allowing for 1.5 HCl, 1.5 H2O: C, 52.04; H, 5.66; N, 7.59; S, 8.68; Found: C, 51.90; H, 5.40; N, 7.40; S, 8.70; MS (MH+). 657.4.
  • 21
  • C13H10N3O2PolS [ No CAS ]
  • [ 91183-71-0 ]
  • C18H19N4O3PolS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; diisopropyl-carbodiimide; In dichloromethane; at 20℃; for 18h; Resin 1F (500 mg; 2.24 mmol) is swollen with CH2Cl2 (2×80 ml) and H-Met-O-tert-Bu hydrochloride (540 mg; 2.24 mmol), dichloromethane (11 ml), DIPEA (0.39 ml; 2.2 mmol), 3-hydroxy-1,2,3-benzotriazin-4-(3H)-one (HOOBT; 360 mg; 2.24 mmol) and 1,3-diisopropylcarbodiimide (DIC) (0.35 ml; 2.4 mmol) are then added. The mixture is stirred for 18 hours at room temperature. The resin is then filtered off, washed successively with DMF (2×), CH2Cl2 (2×), MeOH (2×), CH2Cl2 (2×) and finally dried (572 mg; 94%). [0109] A sample of this resin (100 mg) is cleaved by treatment with a 50/50/10 TFA/CH2Cl2/Et3SiH solution (3 ml) for 2.5 hours. The suspension is filtered and the resin is rinsed with CH2Cl2 (2×). The filtrates are combined and concentrated to give the desired product 1 (22 mg; 37%). [0110] HPLC (C18, lambda 220 nM), 100% H2O to 100% CH2CN (+0.1% TFA) over 8 minutes): purity: 87%. [0111] Mass spectrum (ESI): m/z 405 (MH+).
  • 22
  • [ 858104-55-9 ]
  • [ 91183-71-0 ]
  • N-[4-((2R,3R)-1-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycyl-L-methionine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Method 9; N-1 [4- ( (2R, 3R)-l- (4-fluorophenyl)-3-1 [2- (4-fluorophenyl)-2-oxoethyl] thio}-4-oxoazetidin- 2-yl) phenoxy]acetyl}glycyl-L-methionine; A mixture of 3- (R)-4- (R)-l- (4-Fluorophenyl)-3- [ (4-fluorobenzoyl) methylthio]-4-14- [N- (carboxymethyl) carbamoylmethoxy] phenyl} azetidin-2-one (0.0197g, 0.036 mmol), tert-butyl L-methioninate hydrochloride (0.0144 g, 0.060 mmol) and N-methylmorpholine (0.012 ml, 0. 111 mmol) in DCM (2ml) was stirred at room temperature. TBTU (0.018 g, 0.056 mmol) was added and the mixture was stirred overnight. Trifluoroacetic acid (0.65 ml) was added and after a couple of hours the hydrolysis was complete according to LC-MS. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC on a Kromasil C8-column using a gradient of 5-100% MeCN in 0.15% trifluoroacetic acid buffer as eluent. The solvent was removed under reduced pressure and 0.015 g (61 %) of the title product was obtained. M/z 672.10.
  • 23
  • [ 5070-13-3 ]
  • [ 91183-71-0 ]
  • C16H22N2O6S [ No CAS ]
  • 24
  • [ 858103-94-3 ]
  • [ 91183-71-0 ]
  • [ 13518-40-6 ]
  • C39H45F2N3O7S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 55; N-[4-((2R, 3R)-1-(4-fluorophenyl)-3-[2-(4-fluorophenyl)-2-hydroxyethyl] thio}-4- oxoazetidin-2-yl) phenoxy] acetyl}-D-valyl-L-methionine; N-[4-((2R,3R)-1-(4-Fluorophenyl)-3-[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2- yl) phenoxy] acetyl}-D-valine (13.3 mg, 0.023 mmol), tert-butyl L-methioninate hydrochloride (7.4 mg, 0.031 mmol) and N-methylmorpholine (10, ul, 0.091 mmol) were dissolved in 1 ml. After 5 minutes, TBTU (8.9 mg, 0.028 mmol) was added and the resulting suspension was stirred overnight. Additional tert-butyl L-methioninate hydrochloride (2.1 mg, 0087 mmol), N-methylmorpholine (5, ul, 45, umol) and TBTU (2.1 mg, 6.54 jumol) were added and the mixture was stirred for 2 h. The formation of the ester was confirmed. M/z 768.1 (M-H) and 770.0 (M+H). The yellow suspension was purified on silica gel (1g) and eluted with EtOAc: DCM (15: 85). The pure fractions were concentrated and formic acid (1.5 ml) was added. The solution was stirred at 50C overnight. The solvent was removed under reduced pressure. Toluene was added and removed under reduced pressure. The residue was dissolved in methanol (1 ml) and sodium borohydride (9.9 mg, 0.26 mmol) was added. The resulting reaction mixture was stirred for 10 minutes. Ammonium acetate (18.9 mg) was added and the solvent was removed under reduced pressure. The residue was purified with preparative HPLC on a C8 column. A gradient from 20% to 40 % MeCN in 0.1 M ammonium acetate buffer was used as eluent. After lyophilisation, the title compound was obtained as a white solid was obtained (4.6 mg, 28%). 1H-NMR (400 MHz, DMSO-d6) : 0.75 (d, 3H), 0.79 (d, 3H), 1.79-1. 97 (m, 3H), 1.99 (s, 3H), 2.36-2. 44 (m, 2H), 2.86-2. 92 (m, 2H), 2.24-4. 35 (m, 3H), 4.58 (d, 2H), 4.67-4. 76 (m, 1H), 5.03 (d, 0.5H), 5.5 (d, 0. 5H), 5.63 (t, 1H), 6.95 (d, 2H), 7.05-7. 16 (m, 4H), 7.18-7. 24 (m, 2H), 7.30-7. 38 (m, 2H), 7.82 (d, 1H), 7.37 (d, 1H). M/z : 714.0 (M-1) and 716.1 (M+H).
  • 25
  • [ 91183-71-0 ]
  • [ 1405-86-3 ]
  • [ 1200807-15-3 ]
  • 27
  • [ 91183-71-0 ]
  • [ 53100-44-0 ]
  • C19H32N2O6S [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h; To a solution of HCl·Met-OtBu (242 mg, 1.0 mmol) in DMF (10 ml)was added Et3N (0.15 ml, 1.1 mmol) and Boc-pyroGlu-OH (229 mg,1.0 mol) at 0 C. HOBt (271 mg, 2.0 mmol) and EDC·HCl (287 mg,1.5 mmol) were added and the reaction mixture was stirred for 12 hat room temperature. After the removal of the solvent under reducedpressure, the residue was dissolved in ethyl acetate, and washed with5% NaHCO3 and 10% citric acid, and dried over anhydrous sodiumsulfate. After filtration, the resulting filtrate was concentrated underreduced pressure and white product was precipitated by diethyl etherto give 248 mg of protected dipeptide in 59% yield. The protected dipeptide (198 mg) was treated with 4 M HCl/dioxane at room temperaturefor 3 h to remove the protected groups. After the removal of excessHCl/dioxane, white solid was precipitated by ether to give 90 mg ofdesired product in 73% yield. MS (ESI) m/z: 261.09 [M + H]+ (calcd.261.09).
  • 28
  • C66H71N3O22 [ No CAS ]
  • [ 91183-71-0 ]
  • C67H111N3O19S5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; at 20 - 22℃; for 24h; General procedure: N-Hydroxyphthalimide (3.0-3.5 mmol) and N,N-dicyclohexylcarbodiimide (3.0-3.5 mmol) were added to a solution of glycyrrhizic acid (1.0 mmol) in 20 mL of dioxane or THF at 0-5 C and the mixture was stirred for 1 h at this temperature, then at 20-22 C for 4 h. The precipitated dicyclohexylurea was filtered off, and tert-butyl ester of amino acid hydrochloride (4 mmol) and triethylamine (5-6 mmol) were added to the filtrate. The mixture was kept for 24 h at 20-22 C with occasional stirring. Then the mixture was poured in cold 5% solution of NaHCO3, the precipitate was filtered off, washed with water, dried, and reprecipitated from aqueous ethanol to provide carboxylprotectedconjugates 3, 5, 7, and 9 in 60-65% yield. To remove the ester tert-butyl group the obtained products (0.6-0.8 g) were dissolved in a mixture of methylene chloride and trifluorocetic acid (1 : 1, 10 mL). The mixture was kept for 1 h at 20-22 C, then evaporated in a vacuum and purified by column chromatography on silica gel eluting with a mixture chloroform-methanol-water (300 : 10 : 1, 200 : 10 : 1, 100 : 10 : 1, 50 : 10 : 1, vol). The individual fractions (by TLC) were combined and evaporated.
  • 29
  • C9H13N3O3 [ No CAS ]
  • [ 91183-71-0 ]
  • (S)-tert-butyl 2-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-4-(methylthio)butanoate [ No CAS ]
  • 30
  • [ 91183-71-0 ]
  • [ 530-62-1 ]
  • [ 106015-56-9 ]
  • 31
  • [ 91183-71-0 ]
  • [ 1610768-79-0 ]
  • 32
  • [ 199434-50-9 ]
  • [ 91183-71-0 ]
  • C12H22N2O4S [ No CAS ]
  • 33
  • [ 91183-71-0 ]
  • C12H24N2O3S [ No CAS ]
  • C12H24N2O3S [ No CAS ]
  • 34
  • [ 402-43-7 ]
  • [ 91183-71-0 ]
  • C16H22F3NO2S [ No CAS ]
  • C16H22F3NO2S [ No CAS ]
  • 35
  • [ 91183-71-0 ]
  • FmocHN-L-(NHBoc)Lys-L-Val-L-Met-OtBu [ No CAS ]
 

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