N-t-butoxycarbonyl-leucyl-glycine-pentachlorophenyl ester → Leucyl-glycine-pentachlorophenyl ester.hydrochloride

HRID 1248745Notes

Reaction equation

HRID 1248745 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[C@H:13]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:14]C(OC(C)(C)C)=O)=[C:6]([Cl:28])[C:5]([Cl:29])=[C:4]([Cl:30])[C:3]=1[Cl:31].Cl.C(O)(=O)C>>[ClH:1].[Cl:1][C:2]1[C:7]([O:8][C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[C@H:13]([CH2:22][CH:23]([CH3:24])[CH3:25])[NH2:14])=[C:6]([Cl:28])[C:5]([Cl:29])=[C:4]([Cl:30])[C:3]=1[Cl:31]

Participants

3

Reactant 2

HCID 18598487N-t-butoxycarbonyl-leucyl-glycine-pentachlorophenyl esterHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 18598480Leucyl-glycine-pentachlorophenyl ester.hydrochloride

Procedure

To 31.7 g of the aforesaid ester was added 295 ml of 2.1lN HCl-acetic acid, and the resulting mixture was subjected to reaction for 1.5 hours while protecting the reaction from moisture, whereby leucyl-glycine-pentachlorophenyl ester.hydrochloride was obtained. For purification, the hydrochloride was recrystallized from methanol and ether to obtain 22.6 g (80.7%) of the hydrochloride in a pure form. Mp: 164°-166° C. [α]D26 =+2.85° (C=1, methanol). Rf value in thin layer chromatography; chloroform-methanol-acetic acid (95:5:3) was used as a developing solvent. Rf=0.82 (for color development, ninhydrin reagent was used).

Workup

  1. customthe resulting mixture was subjected to reaction for 1.5 hours
  2. customthe reaction from moisture

Sources & evidence

ORD record
ord-e7b804e87a4c4bf3880ce36e53c2d367
Source dataset
uspto-grants-1985_06
Patent number
US04525576

Reaction notes

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