tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate → tert-Butyl N-[(2R)-2-amino-2-phenylethanoyl]-O-(tert-butyl)-L-serinate

HRID 2377660Notes

Reaction equation

HRID 2377660 reaction equation
C(OC([NH:11][C@H:12]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:13]([NH:15][C@H:16]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:14])=O)C1C=CC=CC=1>CCO.[Pd]>[NH2:11][C@H:12]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:13]([NH:15][C@H:16]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:17][O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:14]

Participants

4

Reactant 1

HCID 69551729tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate

Product 1

HCID 66843016tert-Butyl N-[(2R)-2-amino-2-phenylethanoyl]-O-(tert-butyl)-L-serinateYield 98.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)-O-(tert-butyl)-L-serinate (Method 5; 3.3 g, 6.8 mmol) was dissolved in EtOH (95%, 30 ml) and a cat amount of Pd/C (5%)(50% in water) was added and hydrogenation was performed at atmospheric pressure for 3 hours at room temperature. The reaction mixture was filtered through diatomaceous earth and the solvent was evaporated to give the title compound (2.35 g, 98%). NMR (500 MHz, CD3OD): 1.1 (s, 9H), 1.45 (s, 9H), 3.45-3.8 (m, 2H), 4.5 (t, 1H), 4.55 (s, 1H), 4.85 (s, 2H), 7.3-7.5 (m, 5H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f848409350014ddaa1f907c317c00565
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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