(R)-tert-butyl 2-(2-(benzyloxycarbonylamino)-2-phenylacetamido)acetate → tert-Butyl (R)-(2-amino-2-phenylacetyl)glycinate

HRID 719104Notes

Reaction equation

HRID 719104 reaction equation
C(OC([NH:11][C@@H:12]([C:19](=[O:29])[NH:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)C1C=CC=CC=1>CCO.C1(C)C=CC=CC=1.[Pd]>[C:25]([O:24][C:22]([CH2:21][NH:20][C:19]([C@H:12]([NH2:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:29])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 1

HCID 68452209(R)-tert-butyl 2-(2-(benzyloxycarbonylamino)-2-phenylacetamido)acetate

Product 1

HCID 67006160tert-Butyl (R)-(2-amino-2-phenylacetyl)glycinateYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

(R)-N-Benzyloxycarbonyl-α-[N-(t-butoxycarbonylmethyl)carbamoyl]benzylamine (Method 4; 12.8 g, 32.2 mmol) was dissolved in EtOH (99%, 200 ml) and toluene (50 ml). Pd/C (10%, 0.65 g) was added and hydrogenation was performed at atmospheric pressure for 5.5 hours at room temperature. The reaction mixture was filtered through diatomaceous earth and the solvents were evaporated to give the title compound (8.4 g, 99%). NMR (600 MHz, CDCl3): 1.45 (s, 9H), 3.93 (m, 2H), 4.54 (s, 1H), 7.31–7.42 (m, 5H), 7.51 (brs, 1H).

Workup

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

Sources & evidence

ORD record
ord-115106d942d844c887401f5d53bd7a13
Source dataset
uspto-grants-2006_11
Patent number
US07132416B2

Reaction notes

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