(S)-4-t-Butoxycarbonylamino-5-(biphenyl-4-yl)-pentenoic acid ethyl ester → (S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylaminopentanoic acid ethyl ester

HRID 1655292Notes

Reaction equation

HRID 1655292 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH:5]=[CH:6][C@@H:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C@H:7]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54107369(S)-4-t-Butoxycarbonylamino-5-(biphenyl-4-yl)-pentenoic acid ethyl ester

Product 1

HCID 53829475(S)-5-Biphenyl-4-yl-4-tert-butoxycarbonylaminopentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(S)-4-(t-Butoxycarbonylamino)-5-(biphenyl-4-yl)-pentenoic acid ethyl ester (1.6 g), is dissolved in ethanol and hydrogenated under 48 psi for 2 hours with Pd/C catalyst. The mixture is filtered through Celite and the filtrate is concentrated in vacuo to yield (S)-4-(t-butoxycarbonylamino)-5-(biphenyl-4-yl)-pentanoic acid ethyl ester.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f7e429bdcbe34aad8e958785c0dca47f
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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