HCID 131720162, compound → H-Asp(OtBu)-Ser(tBu)-OtBu

HRID 1376680Notes

Reaction equation

HRID 1376680 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].[H][H]>CO.[Pd]>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:15][O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:8])([CH3:9])[CH3:7]

Participants

5

Reactant 2

HCID 131720162HCID 131720162, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131720161H-Asp(OtBu)-Ser(tBu)-OtBuYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.9 g of Z-Asp(OtBu)-Ser(tBu)-OtBu are hydrogenated in 100 ml of methanol in the presence of 0.1 g of Pd/C 10%. After the theoretical amount of hydrogen has been taken up the mixture is filtered and the filtrate is evaporated to dryness. Chromatography on silica gel with methylene chloride/MeOH (98:2) gives 1.28 g (91%) of H-Asp(OtBu)-Ser(tBu)-OtBu, MS: 389 (M+H)+.

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-d81749011f0d4862a65430206ca5b6cc
Source dataset
uspto-grants-1997_09
Patent number
US05663297

Reaction notes

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