Acetic Acid → 2-(4-Phenacyloxyphenyl)glycine phenacyl ester hydrobromide

HRID 444425Notes

Reaction equation

HRID 444425 reaction equation
[CH2:1]([O:10][C:11](=[O:37])[CH:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[CH:23][CH:22]=1)[NH:13]C(OC(C)(C)C)=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[BrH:38].C(O)(=O)C>C(OCC)(=O)C>[BrH:38].[CH2:1]([O:10][C:11](=[O:37])[CH:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:30])=[CH:23][CH:22]=1)[NH2:13])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 20243679N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester

Product 1

HCID 704567262-(4-Phenacyloxyphenyl)glycine phenacyl ester hydrobromide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-tert-butoxycarbonyl-2-(4-phenacyloxyphenyl)glycin phenacyl ester (1.0 g.) in ethyl acetate (10 ml.) was added a mixture of hydrobromic acid and acetic acid (2 ml., 4:1 v/v), and then the mixture was stirred for half an hour at ambient temperature. The precipitates were collected by filtration and washed with ethyl acetate to give 2-(4-phenacyloxyphenyl)glycine phenacyl ester hydrobromide (830 mg.), which was recrystallized from a mixture of ethanol, methanol and diethyl ether to give the pure crystals (550 mg.), mp 176° to 177° C.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-90ad52b6bd5741c2b604072f609e3489
Source dataset
uspto-grants-1981_04
Patent number
US04264498

Reaction notes

Loading…