L-Phenylalanine → 2,2,2-Trichloroethoxycarbonyl-L-phenylalanine

HRID 1655721Notes

Reaction equation

HRID 1655721 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCCCCC>[Cl:19][C:18]([Cl:21])([Cl:20])[CH2:17][O:16][C:14]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:15]

Participants

5

Reactant 3

HCID 6140L-PhenylalanineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 135061342,2,2-Trichloroethoxycarbonyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

L-phenylalanine was reacted with 2,2,2-trichloroethyl chloroformate in a 2N sodium bicarbonate solution, and after the usual working-up there was obtained the desired acid as crystals, melting point 126° (from methylene chloride/hexane).

Sources & evidence

ORD record
ord-e91db11db4224026b1f0fc484be83637
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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