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

HRID 1656058Notes

Reaction equation

HRID 1656058 reaction equation
C([S:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=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.[NH4+].[OH-]>O1CCCC1>[SH:4][CH2:5][C:6]1([C:16]([NH:18][CH2:19][CH:20]([C:22]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=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

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 88127936N-[[1,2,3,4-Tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Product 1

HCID 88128334N-[[1,2,3,4-Tetrahydro-2-(mercaptomethyl)-2-naphthalenyl]carbonyl]-isoserine, benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve N-[[1,2,3,4-tetrahydro-2-[(acetylthio)methyl]-2-naphthalenyl]carbonyl]-isoserine, benzyl ester (882 mg, 2.00 mmol) in tetrahydrofuran (20 mL) then add NH4OH (1 mL). Stir at ambient temperature under an atmosphere of argon for 24 hours, then concentrate in vacuo. Purify the residue by column chromatography (ethyl acetate:hexane) to give the title compound.

Workup

  1. concentrationconcentrate in vacuo
  2. customPurify the residue by column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-1aea0af2b8144e1890edc2b27b63e5cb
Source dataset
uspto-grants-1993_10
Patent number
US05252601

Reaction notes

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