Hydrochloric Acid → (S)-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-cyclohexyl-acetic acid

HRID 1970619Notes

Reaction equation

HRID 1970619 reaction equation
C[O:2][C:3](=[O:41])[C@@H:4]([NH:11][C:12]([C:14]1[CH:18]=[C:17]([O:19][CH2:20][C:21]([N:23]2[CH2:27][CH2:26][CH2:25][C@H:24]2[C:28](=[O:34])[NH:29][CH:30]2[CH2:33][CH2:32][CH2:31]2)=[O:22])[N:16]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:15]=1)=[O:13])[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-].[Li+].Cl>C1COCC1.O>[CH:30]1([NH:29][C:28]([C@@H:24]2[CH2:25][CH2:26][CH2:27][N:23]2[C:21](=[O:22])[CH2:20][O:19][C:17]2[N:16]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:15]=[C:14]([C:12]([NH:11][C@@H:4]([CH:5]3[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]3)[C:3]([OH:41])=[O:2])=[O:13])[CH:18]=2)=[O:34])[CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66856691(S)-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-cyclohexyl-acetic acid methyl ester

Product 1

HCID 66855107(S)-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-cyclohexyl-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 428 mg (S)-({5-[2-((S)-2-Cyclobutylcarbamoyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-cyclohexyl-acetic acid methyl ester in 20 ml THF and 5 ml water were added 30 mg lithium hydroxide at 0° C. After stirring for 4 h it was acidified with 1 N HCl and concentrated in vacuo to give the crude product as colorless oil. Yield: 380 mg.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-784d1a490b454b4caaf6a421fae65157
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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