Benzyl[(1S)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate → N-{3-[(tert-Butoxycarbonyl)amino]-2-hydroxypropyl}-L-serinamide

HRID 269627Notes

Reaction equation

HRID 269627 reaction equation
C(OC(=O)[NH:10][C@@H:11]([CH2:27][OH:28])[C:12]([NH:14][CH2:15][CH:16]([OH:26])[CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:13])C1C=CC=CC=1>C(O)C.[Pd]>[C:22]([O:21][C:19]([NH:18][CH2:17][CH:16]([OH:26])[CH2:15][NH:14][C:12](=[O:13])[C@H:11]([CH2:27][OH:28])[NH2:10])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 1

HCID 131727151Benzyl[(1S)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate

Product 1

HCID 86619427N-{3-[(tert-Butoxycarbonyl)amino]-2-hydroxypropyl}-L-serinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

131 mg (0.318 mmol) of benzyl[(1S)-2-({3-[(tert-butoxycarbonyl)amino]-2-hydroxypropyl}amino)-1-(hydroxymethyl)-2-oxoethyl]carbamate (Example 100A) are dissolved in 20 ml of ethanol. 20 mg of palladium on activated carbon (10%) are added thereto, and the mixture is hydrogenated under atmospheric pressure for 15 h. The reaction mixture is filtered through prewashed kieselguhr, and the filtrate is concentrated in vacuo on a rotary evaporator. The crude product is reacted without further purification.

Workup

  1. filtrationThe reaction mixture is filtered through prewashed kieselguhr
  2. concentrationthe filtrate is concentrated in vacuo on a rotary evaporator
  3. customThe crude product is reacted without further purification

Sources & evidence

ORD record
ord-cf54cee1f4db40239d57e0ac1d8884b1
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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