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 1908627Notes

Reaction equation

HRID 1908627 reaction equation
C[O:2][C:3](=[O:36])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[N:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[OH-].[Na+].Cl>C1COCC1>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:23][C:24](=[O:29])[C:25]([CH3:26])([CH3:27])[CH3:28])[N:19]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:18]=1)=[O:16])[C:3]([OH:36])=[O:2])([CH3:11])([CH3:12])[CH3:13]

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 ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.4 g of (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 15 ml of THF, 6.5 ml of a 1 M aqueous NaOH solution was added. After stirring at RT upon completion of the reaction the mixture was acidified to pH 2 with diluted aqueous hydrochloric acid and extracted with DCM (3×100 ml). The combined organic phases were dried over MgSO4 and the solvents were removed under reduced pressure to yield a crystalline solid. Yield: 3.4 g

Workup

  1. extractionextracted with DCM (3×100 ml)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. customthe solvents were removed under reduced pressure
  4. customto yield a crystalline solid

Sources & evidence

ORD record
ord-77dde2e1a32140fba64132b8e909675a
Source dataset
uspto-grants-2013_12
Patent number
US08598179B2

Reaction notes

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