Triethylamine → 2,4,5-Trichlorophenyl 3-phenyl-N-((phenylmethoxy)carbonyl)-L-alaninate

HRID 1283778Notes

Reaction equation

HRID 1283778 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([OH:22])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[C:34]([Cl:38])=[CH:33][C:32]=1OC(ON=C(C#N)C(OCC)=O)=O>C(OCC)(=O)C>[Cl:30][C:31]1[CH:36]=[C:35]([Cl:37])[C:34]([Cl:38])=[CH:33][C:32]=1[O:21][C:20](=[O:22])[C@H:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 54542381Ethyl 2-(2,4,5-trichlorophenyl)oxycarbonyloxyimino-2-cyanoacetate

Product 1

HCID 972532,4,5-Trichlorophenyl 3-phenyl-N-((phenylmethoxy)carbonyl)-L-alaninateYield 79.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyloxycarbonyl-L-phenylalanine (1.5 g) and triethylamine (0.7 ml) in ethyl acetate (20 ml), ethyl 2-(2,4,5-trichlorophenyl)oxycarbonyloxyimino-2-cyanoacetate (1.9 g) is added, and the resulting mixture is stirred at room temperature for 4 hours. The reaction mixture is treated as in Example 16 to give N-benzyloxycarbonyl-L-phenylalanine 2,4,5-trichlorophenyl ester (1.9 g). M.P. 139° - 140°C.

Workup

  1. additionThe reaction mixture is treated as in Example 16

Sources & evidence

ORD record
ord-0650c752bb8f4251b61819bd8087a6a8
Source dataset
uspto-grants-1976_08
Patent number
US03976635

Reaction notes

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