Pentachlorophenol → N-benzhydryloxycarbonylglycine pentachlorophenyl ester

HRID 65604

Reaction equation

HRID 65604 reaction equation
[CH:1]([O:14][C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[C:28](O)=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[Cl:22][C:23]1[C:28]([O:20][C:19](=[O:21])[CH2:18][NH:17][C:15]([O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:16])=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 22757153N-benzhydryloxycarbonylglycine

Product 1

HCID 22757140N-benzhydryloxycarbonylglycine pentachlorophenyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture consisting of 10 g. of N-benzhydryloxycarbonylglycine [this compound is reported in J. Am. Chem. Soc., 87, 3969 (1965)], 9.4 g. of pentachlorophenol, and 150 ml. of ethyl acetate, at 5° C., is added 7.3 g. of dicyclohexylcarbodiimide, and the resulting solution is kept at 5° C. for 5 hours and filtered. The filtrate is evaporated, and the residue is triturated with petroleum ether to give a solid precipitate of N-benzhydryloxycarbonylglycine pentachlorophenyl ester, which is isolated and dried; m.p. 171°-172° C.

Workup

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. customthe residue is triturated with petroleum ether

Sources & evidence

ORD record
ord-1b1df8381d714521a0ca34860fcea2ff
Source dataset
uspto-grants-1978_12
Patent number
US04128540

Linked notes

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