Hydrochloric Acid → (S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester

HRID 1908647Notes

Reaction equation

HRID 1908647 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:38])[C@@H:6]([NH:16][C:17]([C:19]1[CH:23]=[C:22]([O:24][CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])[N:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:20]=1)=[O:18])[CH2:7][CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].Cl>C1COCC1>[C:12]([O:11][C:9](=[O:10])[CH2:8][CH2:7][C@H:6]([NH:16][C:17]([C:19]1[CH:23]=[C:22]([O:24][CH2:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:29])[CH3:30])[N:21]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:20]=1)=[O:18])[C:5]([OH:38])=[O:4])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66920060(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester

Product 1

HCID 66919946(S)-2-{[5-(3,3-Dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl esterYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 M aqueous NaOH was added to a solution of 11.8 g (S)-2-{[5-(3,3-dimethyl-2-oxo-butoxy)-1-phenyl-1H-pyrazole-3-carbonyl]-amino}-pentanedioic acid 5-tert-butyl ester 1-methyl ester in 31 ml THF at RT. After 2 h 5 M HCl was added to bring the reaction mixture to pH 5. Extraction with DCM yielded the product as colorless solid (10.8 g).

Workup

  1. extractionExtraction with DCM

Sources & evidence

ORD record
ord-7b21987fc34d4a6cb740de6d4d9c85a0
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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