Z-Asn-Phe-psi (CH(OH)CH2N)Pro-OtBu → N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester

HRID 1757714Notes

Reaction equation

HRID 1757714 reaction equation
[C:1]([O:5][C:6](=[O:42])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:41])[C@@H:14]([NH:22][C:23](=[O:40])[C@H:24]([CH2:36][C:37](=[O:39])[NH2:38])[NH:25]C(OCC1C=CC=CC=1)=O)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6](=[O:42])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[CH2:12][C@@H:13]([OH:41])[C@@H:14]([NH:22][C:23](=[O:40])[C@H:24]([CH2:36][C:37](=[O:39])[NH2:38])[NH2:25])[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 451719Z-Asn-Phe-psi (CH(OH)CH2N)Pro-OtBu

Product 1

HCID 70041604N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl esterYield 84.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A solution of 1.75 g of N-[3(S)-[[N-(benzyloxycarbonyl)-L-asparaginyl] amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester in 100 ml ofethanol was hydrogenated over 10% palladium-on-carbon for 64 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residual gum was partitioned between ethyl acetate and 2M hydrochloric acid. The aqueous phase was made basic with dilute sodium hydroxide solution and extracted with ethyl acetate. The ethyl acetate extract was evaporated to give 1.14 g of N-[3(S)-[[L-asparaginyl]amino]-2(R)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester as a white, solid foam; MS: m/e 449 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residual gum was partitioned between ethyl acetate and 2M hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. customwas evaporated

Sources & evidence

ORD record
ord-a311558e17454675915c9765d5cd23ca
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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