Lithium Hydroxide → N-[[1,2,3,4-Tetrahydro-2-(mercaptomethyl)-2-naphthalenyl]carbonyl]-isoserine

HRID 1656057Notes

Reaction equation

HRID 1656057 reaction equation
C([S:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])[OH:21])=[O:17])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)(=O)C.[Li+].[OH-]>O1CCCC1>[SH:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([OH:24])=[O:23])[OH:21])=[O:17])[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Product 1

HCID 19789942N-[[1,2,3,4-Tetrahydro-2-(mercaptomethyl)-2-naphthalenyl]carbonyl]-isoserine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve N-[[1,2,3,4-tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester (4.41 g, 10.0 mmol) in deoxygenated tetrahydrofuran (50 mL). To this solution add 1N LiOH (30 mL, 30.0 mmol) and stir under an atmosphere of argon for 4 hours. Concentrate the solution in vacuo then purify the residue by column chromatography (acetic acid:ethyl acetate:hexane) to give the title compound.

Workup

  1. concentrationConcentrate the solution in vacuo
  2. customthen purify the residue by column chromatography (acetic acid:ethyl acetate:hexane)

Sources & evidence

ORD record
ord-b20f51fbf8bc4218bddc10f10bc39db0
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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