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

HRID 2377658Notes

Reaction equation

HRID 2377658 reaction equation
C(OC([NH:11][C@H:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:14])=O)C1C=CC=CC=1>CCO.C1(C)C=CC=CC=1.[Pd]>[NH2:11][C@H:12]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:13]([NH:15][CH2:16][C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])=[O:14]

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

tert-Butyl N-((2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoyl)glycinate (Method 3; 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 hours 30 minutes 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): 1.45 (s, 9 H), 3.93 (m, 2 H), 4.54 (s, 1 H), 7.31-7.42 (m, 5 H), 7.51 (br s, 1 H)

Workup

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

Sources & evidence

ORD record
ord-6d8346c536f04530a81d13d84955a254
Source dataset
uspto-grants-2008_12
Patent number
US07470678B2

Reaction notes

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