HCID 53768474, compound → HCID 18603046, compound

HRID 1981929Notes

Reaction equation

HRID 1981929 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9](=[O:37])[CH2:10][NH:11][C:12](=[O:36])[C@H:13]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:14][C:15](=[O:28])[C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2C(OC(C)(C)C)=O)=[C:6]([Cl:38])[C:5]([Cl:39])=[C:4]([Cl:40])[C:3]=1[Cl:41]>Cl.C(OCC)(=O)C>[ClH:1].[Cl:38][C:6]1[C:7]([O:8][C:9](=[O:37])[CH2:10][NH:11][C:12](=[O:36])[C@H:13]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:14][C:15](=[O:28])[C@@H:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)=[C:2]([Cl:1])[C:3]([Cl:41])=[C:4]([Cl:40])[C:5]=1[Cl:39]

Participants

3

Reactant 1

HCID 53768474HCID 53768474, compound

Product 1

HCID 18603046HCID 18603046, compound

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

N-t-Butoxycarbonyl-prolyl-phenylalanyl-glycine pentachlorophenyl ester in an amount of 36.4 g was dissolved in 410 ml of 2.2 N HCl-ethyl acetate. A precipitate was produced soon. After the reaction at room temperature for 1.5 hours, the precipitate was filtered, washed with ether and recrystallized from 1.2 l of methanol to give crystals of prolyl-phenylalanyl-glycine pentachlorophenyl ester.hydrochloride in yield of 21.5 g (65.2%) having a melting point of 182°-184° C. and Rf=0.78 (TLC, chloroform: methanol: acetic acid=85:5:3 by volume).

Workup

  1. customA precipitate was produced soon
  2. customAfter the reaction at room temperature for 1.5 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with ether
  5. customrecrystallized from 1.2 l of methanol

Sources & evidence

ORD record
ord-46c1f3950c8c482e9c1c48626cc0645a
Source dataset
uspto-grants-1986_06
Patent number
US04594409

Reaction notes

Loading…