Methanethiol → Ethyl 3-amino-2-[[[2'-[[[(propylamino)-carbonyl]-amino]sulfonyl]-(1,1'-biphenyl)-4-yl]-methyl]-(1-oxopentyl)-amino]-3-(methylthio)-2-propenoate

HRID 260548Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:38])[CH:5]([C:36]#[N:37])[N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([NH:29][C:30]([NH:32][CH2:33][CH2:34][CH3:35])=[O:31])(=[O:28])=[O:27])=[CH:16][CH:15]=1)[C:7](=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11])[CH3:2].C(N(CC)CC)C.[CH3:46][SH:47]>ClCCl>[NH2:37][C:36]([S:47][CH3:46])=[C:5]([N:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([NH:29][C:30]([NH:32][CH2:33][CH2:34][CH3:35])=[O:31])(=[O:28])=[O:27])=[CH:16][CH:15]=1)[C:7](=[O:12])[CH2:8][CH2:9][CH2:10][CH3:11])[C:4]([O:3][CH2:1][CH3:2])=[O:38]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 8.5 g of the product of Stage B and 2.4 ml of triethylamine in 100 ml of dichloromethane was saturated with methanethiol by sweeping through the stirred solution cooled to -20° C. The temperature was allowed to rise and then the solution was maintained under a nitrogen pressure of 10 bars at 40° C. for 48 hours. After concentration, the residue was purified by chromatography on silica (eluant: dichloromethane-MeOH 20-1) to obtain 8.0 g of the expected product with an Rf (SiO2, dichloromethane-MeOH20-1)=0.39.

Workup

temperaturethe solution was maintained under a nitrogen pressure of 10 bars at 40° C. for 48 hours
concentrationAfter concentration
customthe residue was purified by chromatography on silica (eluant: dichloromethane-MeOH 20-1)

Sources & evidence

ORD record: ord-81b7d7e2528b4444ad5ef9bbd0a6e96e
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05527919

Reaction notes

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