Hydrochloric Acid → epsilon-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester hydrochloride

HRID 979447Notes

Reaction equation

HRID 979447 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:39])[CH2:10][N:11]([C:13](=[O:38])[C@:14](C(OC(C)(C)C)=O)([CH2:16][CH2:17][CH2:18][CH:19]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[NH2:20])[NH2:15])[CH3:12].[ClH:41]>C(OCC)(=O)C>[ClH:41].[CH3:1][O:2][C:3](=[O:40])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:39])[CH2:10][N:11]([C:13](=[O:38])[C@H:14]([CH2:16][CH2:17][CH2:18][CH:19]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[NH2:20])[NH2:15])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86741546alpha-tertiary butyloxycarbonyl-epsilon-benzyloxycarbonyl-L-lysylsarcosyl-L-proline methyl ester

Product 1

HCID 70444626epsilon-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The reaction mixture consequently formed was filtered. The filtrate was concentrated under a vacuum. The residue of the concentration was dissolved in 50 ml of ethyl acetate and the resultant solution was filtered. The filtrate was washed with an aqueous 10% citric acid solution, an aqueous 5% sodium hydrogen carbonate solution, and water sequentially in the order mentioned and dried with anhydrous sodium sulfate. The dried substance was distilled under a vacuum to expel the solvent. The residue was solidified with n-hexane to afford 5.05 g of α-tertiary butyloxycarbonyl-ε-benzyloxycarbonyl-L-lysyl-sarcosyl-L-proline methyl ester (melting point 45° to 48° C., yield 79%). This ester was dissolved in 80 ml of a solution prepared by dissolving dry hydrogen chloride gas in ethyl acetate and adjusting the concentration to 3.5N and then left standing for reaction at room temperature for one hour.

Workup

  1. customprepared
  2. concentrationthe concentration to 3.5N
  3. waitleft
  4. customstanding for reaction at room temperature for one hour

Sources & evidence

ORD record
ord-e2604396b73e49c593a4d92b047b9dba
Source dataset
uspto-grants-1987_05
Patent number
US04668397

Reaction notes

Loading…