Structure of 87860-35-3
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 87860-35-3 |
Formula : | C9H12O2 |
M.W : | 152.19 |
SMILES Code : | C[C@@H](CO)OC1=CC=CC=C1 |
MDL No. : | MFCD30164055 |
InChI Key : | LOJHHQNEBFCTQK-QMMMGPOBSA-N |
Pubchem ID : | 10942641 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Ru(H)2{(R)-Tol-BINAP{R,R}-dpen}; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 22℃; under 3040.2 Torr; for 0.333333h;Glovebox; | General procedure: 0.01 mmol (8.1 mg) of RuCl2{(R,R)(Ph2PCH(Ph)CH(Me)NH2}2 (12a), and 0.15 mmol (16.8 mg) of KOtBu were weighed out into two separate NMR tubes in a glove box. 1 mL of freshly distilled THF was then added to each of the NMR tubes and then shaken to dissolve the compounds. A low-pressure glass reactor was then charged with 0.5 mmol of amide and then purged for 10 min with H2. The catalyst precursor solution was then cannulated into the reactor under H2 followed by KOtBu solution and a 2 mL THF wash. The reactor was then pressurized to 4 atm H2. The reaction was then monitored every 20 min by removing a sample and recording the 1H NMR. Several amides and catalysts have been screened using this reaction, and determined the enantiomeric excess of the product alcohols. The data obtained is summarized in table 7, below. Percentage conversion was determined by 1H NMR. Percentage enantiomeric excess (ee) was determined by HPLC using CHIRALPAK TM IB Column, reaction conditions: 4 atm H2, room temperature (22 C.), [Substrate]=0.125 M (4 mL THF). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas cepacia lipase; In aq. phosphate buffer; isopropyl alcohol; at 27℃;pH 7.0;Resolution of racemate; Enzymatic reaction; | General procedure: 10 mL of a mixed solution of crude PcL powder (10 mg mL-1), substrate (ester of chiral primary alcohol, 100 mmol L-1) and PBS (phosphate buffer solution, 100 mmol L-1, pH 7.0, including 10% V/V isopropanol as co-solvent) was added into a 20 mL flask incubated at 27C (300 K) under 200 rpm stirring. The reaction time was controlled as the conversion ratio was between 20 and 30%. The product was extracted by an equal volume of n-octanol. Substrates with aryl groups (2-7, 10-14) were analyzed by an Agilent 1100 HPLC equipped with an Chiralpak AD-H column, whereas those without an aryl group (1, 8 and 9) were analyzed by an HP 1890 GC equipped with a Varian CP-Cyclodextrin-B-2, 3, 6-M-19 capillary GC column. The initial reaction rate = c·[Ester]0·V/Δt, where c is the conversion of the substrate, herein c should be less than 5%; [Ester]0 is the initial molar concentration of the substrate (100 mmol L-1); V is the volume of the reactant (10 mL); and Δt is the reaction time. The enantioselectivity ratio (E value) was calculated according to Chen et al. [18]: E = ln{1 - c(1 + eep)}/ln{1-c(1 - eep)}, where c is the conversion of the substrate; and eep is the enantiomer excess, eep= |[(S)-alcohol] - [(R)-alcohol]|/[(S)-alcohol] + [(R)-alcohol] × 100%. In the formulas, the quantity in the square brackets denotes molar concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas cepacia lipase; In aq. phosphate buffer; isopropyl alcohol; at 27℃;pH 7.0;Resolution of racemate; Enzymatic reaction; | General procedure: 10 mL of a mixed solution of crude PcL powder (10 mg mL-1), substrate (ester of chiral primary alcohol, 100 mmol L-1) and PBS (phosphate buffer solution, 100 mmol L-1, pH 7.0, including 10% V/V isopropanol as co-solvent) was added into a 20 mL flask incubated at 27C (300 K) under 200 rpm stirring. The reaction time was controlled as the conversion ratio was between 20 and 30%. The product was extracted by an equal volume of n-octanol. Substrates with aryl groups (2-7, 10-14) were analyzed by an Agilent 1100 HPLC equipped with an Chiralpak AD-H column, whereas those without an aryl group (1, 8 and 9) were analyzed by an HP 1890 GC equipped with a Varian CP-Cyclodextrin-B-2, 3, 6-M-19 capillary GC column. The initial reaction rate = c·[Ester]0·V/Δt, where c is the conversion of the substrate, herein c should be less than 5%; [Ester]0 is the initial molar concentration of the substrate (100 mmol L-1); V is the volume of the reactant (10 mL); and Δt is the reaction time. The enantioselectivity ratio (E value) was calculated according to Chen et al. [18]: E = ln{1 - c(1 + eep)}/ln{1-c(1 - eep)}, where c is the conversion of the substrate; and eep is the enantiomer excess, eep= |[(S)-alcohol] - [(R)-alcohol]|/[(S)-alcohol] + [(R)-alcohol] × 100%. In the formulas, the quantity in the square brackets denotes molar concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas cepacia lipase; In aq. phosphate buffer; isopropyl alcohol; at 27℃;pH 7.0;Resolution of racemate; Enzymatic reaction; | General procedure: 10 mL of a mixed solution of crude PcL powder (10 mg mL-1), substrate (ester of chiral primary alcohol, 100 mmol L-1) and PBS (phosphate buffer solution, 100 mmol L-1, pH 7.0, including 10% V/V isopropanol as co-solvent) was added into a 20 mL flask incubated at 27C (300 K) under 200 rpm stirring. The reaction time was controlled as the conversion ratio was between 20 and 30%. The product was extracted by an equal volume of n-octanol. Substrates with aryl groups (2-7, 10-14) were analyzed by an Agilent 1100 HPLC equipped with an Chiralpak AD-H column, whereas those without an aryl group (1, 8 and 9) were analyzed by an HP 1890 GC equipped with a Varian CP-Cyclodextrin-B-2, 3, 6-M-19 capillary GC column. The initial reaction rate = c·[Ester]0·V/Δt, where c is the conversion of the substrate, herein c should be less than 5%; [Ester]0 is the initial molar concentration of the substrate (100 mmol L-1); V is the volume of the reactant (10 mL); and Δt is the reaction time. The enantioselectivity ratio (E value) was calculated according to Chen et al. [18]: E = ln{1 - c(1 + eep)}/ln{1-c(1 - eep)}, where c is the conversion of the substrate; and eep is the enantiomer excess, eep= |[(S)-alcohol] - [(R)-alcohol]|/[(S)-alcohol] + [(R)-alcohol] × 100%. In the formulas, the quantity in the square brackets denotes molar concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas cepacia lipase; In aq. phosphate buffer; isopropyl alcohol; at 27℃;pH 7.0;Resolution of racemate; Enzymatic reaction; | General procedure: 10 mL of a mixed solution of crude PcL powder (10 mg mL-1), substrate (ester of chiral primary alcohol, 100 mmol L-1) and PBS (phosphate buffer solution, 100 mmol L-1, pH 7.0, including 10% V/V isopropanol as co-solvent) was added into a 20 mL flask incubated at 27C (300 K) under 200 rpm stirring. The reaction time was controlled as the conversion ratio was between 20 and 30%. The product was extracted by an equal volume of n-octanol. Substrates with aryl groups (2-7, 10-14) were analyzed by an Agilent 1100 HPLC equipped with an Chiralpak AD-H column, whereas those without an aryl group (1, 8 and 9) were analyzed by an HP 1890 GC equipped with a Varian CP-Cyclodextrin-B-2, 3, 6-M-19 capillary GC column. The initial reaction rate = c·[Ester]0·V/Δt, where c is the conversion of the substrate, herein c should be less than 5%; [Ester]0 is the initial molar concentration of the substrate (100 mmol L-1); V is the volume of the reactant (10 mL); and Δt is the reaction time. The enantioselectivity ratio (E value) was calculated according to Chen et al. [18]: E = ln{1 - c(1 + eep)}/ln{1-c(1 - eep)}, where c is the conversion of the substrate; and eep is the enantiomer excess, eep= |[(S)-alcohol] - [(R)-alcohol]|/[(S)-alcohol] + [(R)-alcohol] × 100%. In the formulas, the quantity in the square brackets denotes molar concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pseudomonas cepacia lipase; In aq. phosphate buffer; isopropyl alcohol; at 27℃;pH 7.0;Resolution of racemate; Enzymatic reaction; | General procedure: 10 mL of a mixed solution of crude PcL powder (10 mg mL-1), substrate (ester of chiral primary alcohol, 100 mmol L-1) and PBS (phosphate buffer solution, 100 mmol L-1, pH 7.0, including 10% V/V isopropanol as co-solvent) was added into a 20 mL flask incubated at 27C (300 K) under 200 rpm stirring. The reaction time was controlled as the conversion ratio was between 20 and 30%. The product was extracted by an equal volume of n-octanol. Substrates with aryl groups (2-7, 10-14) were analyzed by an Agilent 1100 HPLC equipped with an Chiralpak AD-H column, whereas those without an aryl group (1, 8 and 9) were analyzed by an HP 1890 GC equipped with a Varian CP-Cyclodextrin-B-2, 3, 6-M-19 capillary GC column. The initial reaction rate = c·[Ester]0·V/Δt, where c is the conversion of the substrate, herein c should be less than 5%; [Ester]0 is the initial molar concentration of the substrate (100 mmol L-1); V is the volume of the reactant (10 mL); and Δt is the reaction time. The enantioselectivity ratio (E value) was calculated according to Chen et al. [18]: E = ln{1 - c(1 + eep)}/ln{1-c(1 - eep)}, where c is the conversion of the substrate; and eep is the enantiomer excess, eep= |[(S)-alcohol] - [(R)-alcohol]|/[(S)-alcohol] + [(R)-alcohol] × 100%. In the formulas, the quantity in the square brackets denotes molar concentration. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12.99% | With diisopropyl (E)-azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; | To a stiired solution of isopropyl (S)-2-(tert-butoxy)-2-(4'-(4,4- dimethylpiperidin-l-yl)-5-hydroxy-6'-methyl-[2,3'-bipyridin]-5'-yl)acetate (60 mg, 0.128 mmol), (S)-2-phenoxypropan-l-ol (38.9 mg, 0.256 mmol) and triphenylphosphine (67.0 mg, 0.256 mmol) in THF (5 mF) was added diisopropyl diazene-l,2-dicarboxylate (51.7 mg, 0.256 mmol) at 0 C. Then, the reaction mixture was stirred at rt overnight and solvent was removed under reduced pressure. H2O (100 ml) and ethyl acetate (150 mF) were added. The organic layer was separated, dried over Na2SC>4, and concentrated. The residue was purified by prep-TLC (pet. ether/EtOAc; 2: 1) to afford isopropyl (S)-2-(tert-butoxy)-2-(4'-(4,4- dimethylpiperidin-l-yl)-6'-methyl-5-((S)-2-phenoxypropoxy)-[2,3'-bipyridin]-5'-yl)acetate (10 mg, 0.016 mmol, 12.99 % yield) as a yellow oil. LC-MS: 604.2 [M+H], Retention time (0.01% NH4HCO3) = 2.66 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.2% | With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 16.0h; | To an ice-cooled solution of (S)-2-phenoxypropan-l-ol (1 1.29 mg, 0.074 mmol) in DMF (3 mF) was added the NaH (8.90 mg, 0.223 mmol) in one portion. Isopropyl (S)-2- (tert-butoxy)-2-(4-(4,4-dimethylpiperidin-l-yl)-6'-fluoro-6-methyl-[3,3'-bipyridin]-5- yl)acetate (35 mg, 0.074 mmol) in DMF (1 mF) was added and the mixture was stirred at rt for addtional 16 h. Then, pH was adjusted to ~7 with 1N HC1. The mixture was filtered and subjected to prep-HPFC purification {Instrument Gilson 281 (PHG-009; Column: Xtimate Prep C18 OBD, 2l .2x 250 mm, 10 pm; Mobile Phase A: Water (10 mmol NH4HCO3); B: MeCN; Gradient: 55-63%B in 8.0 min, stop at 13.0 min;Flow Rate (ml/min) 30.00} to give the desired product (S)-2-(tert-butoxy)-2-(4-(4,4-dimethylpiperidin-l-yl)-6-methyl-6'-((S)-2- phenoxypropoxy)-[3,3'-bipyridin]-5-yl)acetic acid (10.8 mg, 0.019 mmol, 25.2 % yield). FC- MS: 562.3 [M+H], Retention time (0.0l% NH4HCC>3) = 1.62 min. NMR (400 MHz, MeOD) d 8.27-8.04 (m, 2H), 7.69-7.68 (m, 1H), 7.28 (t, J= 8.0 Hz, 2H), 7.11-6.79 (m, 4H), 5.77 (s, 1H), 4.90-4.86 (m, 1H), 4.57 (dd, J= 11.2, 6.2 Hz, 1H), 4.46 (dd, = 11.2, 6.2 Hz, 1H), 3.15-3.14 (m, 2H), 2.74-2.73 (m, 2H), 2.66 (s, 3H), 1.45-1.43 (m, 7H), 1.21 (s, 9H), 0.91 (s, 6H). |
Tags: 87860-35-3 synthesis path| 87860-35-3 SDS| 87860-35-3 COA| 87860-35-3 purity| 87860-35-3 application| 87860-35-3 NMR| 87860-35-3 COA| 87860-35-3 structure
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