(S)-4-(4-Benzyl-2H-tetrazol-5-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester → (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid

HRID 1185521Notes

Reaction equation

HRID 1185521 reaction equation
C([O:8][C:9](=[O:33])[C@@H:10]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:11][CH2:12][C:13]1[N:14](CC2C=CC=CC=2)[NH:15][NH:16][N:17]=1)C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:29]([O:28][C:26]([NH:25][C@@H:10]([CH2:11][CH2:12][C:13]1[N:14]=[N:15][NH:16][N:17]=1)[C:9]([OH:33])=[O:8])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 1

HCID 66854446(S)-4-(4-Benzyl-2H-tetrazol-5-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester

Product 1

HCID 66855300(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-(1H-1,2,3,4-tetrazol-5-yl)butanoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.63 g (S)-4-(4-benzyl-2H-tetrazol-5-yl)-2-tert-butoxycarbonylamino-butyric acid benzyl ester in 400 ml ethyl acetate were added 800 mg Pd(OH)2/C (10%) and the suspension stirred under an atmosphere of hydrogen (4 bar) for 12 h. The reaction mixture was filtrated over a plug of Celite® and washed with ethyl acetate. Yield: 2.84 g colorless solid.

Workup

  1. filtrationThe reaction mixture was filtrated over a plug of Celite®
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-172e07c8c2e94fba81f16e38f4f69f58
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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