Water → 4-N-(Carboxymethyl)-6-[carboxy-3-phenylpropylamino]-perhydro-1,4-thiazepin-5-one

HRID 1981892Notes

Reaction equation

HRID 1981892 reaction equation
[C:1]([CH2:5][N:6]1[C:12](=[O:13])[CH:11]([N:14]([C:24]([O:26]CC)=[O:25])[CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][S:9][CH2:8][CH2:7]1)([O:3]C)=[O:2].O>CO.[OH-].[Na+]>[C:1]([CH2:5][N:6]1[C:12](=[O:13])[CH:11]([N:14]([C:24]([OH:26])=[O:25])[CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:10][S:9][CH2:8][CH2:7]1)([OH:3])=[O:2]

Participants

5

Reactant 2

HCID 962WaterHCID 233180554-N-(Carbomethoxymethyl)-6-(carboethoxy-3-phenylpropylamino)-perhydro-1,4-thiazepin-5-one

Product 1

HCID 233180504-N-(Carboxymethyl)-6-[carboxy-3-phenylpropylamino]-perhydro-1,4-thiazepin-5-oneYield 94.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-[Carbomethoxymethyl]-6-[carboethoxy-3-phenyl propylamino]-perhydro-1,4-thiazepin-5-one (0.1 g) is dissolved in 1.5 ml of methanol and 0.5 ml of 1M sodium hydroxide. At the end of 4 hours at room temperature, 2 ml of water is added. The resulting solution is loaded onto a column of Dowex-50 resin (on the proton cycle). After thorough washing with water, the column is developed with 5% pyridine. The eluent is lyophilized to yield the product as a white solid (0.085 g). The sample analyzes for C17H23N2O5S.1/2H2O.

Workup

  1. washAfter thorough washing with water

Sources & evidence

ORD record
ord-7283a2477c5c46f88a0849511403836f
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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