Ammonia → H-D-Phg-NH2

HRID 2052263Notes

Reaction equation

HRID 2052263 reaction equation
C([N:3](CC)CC)C.[NH:8]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@@H:9]([C:16](O)=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(Cl)(=O)OCC.N>C(Cl)(Cl)Cl>[NH:8]([C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[C@@H:9]([C:16]([NH2:3])=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 87183(R)-(((Phenylmethoxy)carbonyl)amino)phenylacetic acid

Product 1

HCID 14371254H-D-Phg-NH2Yield 49.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

11.6 ml (84 mmoles) of triethylamine are added to a solution of 24.0 g (84 mmoles) of Z-D-Phg-OH in 170 ml of chloroform, and 8.9 ml (84 mmoles) of ethyl chlorocarbonate are added dropwise to the mixture at -10° C. The solution of the mixed anhydride is stirred for additional 10 minutes at -10° C., thereafter cooling is stopped, and gaseous ammonia is introduced into the mixture for one hour. Next day the reaction mixture is evaporated in vacuo, and the solid residue is isolated with water. The crude product is crystallized from ethanol. 11.8 g (49.4%) of Z-D-Phg-NH2 are obtained; the chromatographically uniform substance melts at 171°-173° C. Rf4 : 0.75, [α]D =-76.8° (c=1.0, in dimethyl formamide).

Workup

  1. additionare added dropwise to the mixture at -10° C
  2. temperaturecooling
  3. customNext day the reaction mixture is evaporated in vacuo
  4. customthe solid residue is isolated with water
  5. customThe crude product is crystallized from ethanol

Sources & evidence

ORD record
ord-4f161cd6806b4b81995c8586725f74dd
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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