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

HRID 458929Notes

Reaction equation

HRID 458929 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 85; 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 min 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, 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-ba28c5aa73b14b7f9a97e8aeb0b10cb0
Source dataset
uspto-grants-2007_03
Patent number
US07192945B2

Reaction notes

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