Water → 7-[[[2-[(Diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxyimino) acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)-methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4-methoxyphenyl)methyl Ester

HRID 1196850Notes

Reaction equation

HRID 1196850 reaction equation
C(OP(NC1SC=C(/C(=N/OC)/C(O)=O)N=1)(OCC)=O)C.Cl[CH2:23][C:24]1[CH2:31][S:30][CH:29]2[N:26]([C:27](=[O:53])[CH:28]2[NH:32][C:33](=[O:52])[C:34]([C:38]2[N:39]=[C:40]([NH:43][P:44]([O:49][CH2:50][CH3:51])([O:46][CH2:47][CH3:48])=[O:45])[S:41][CH:42]=2)=[N:35][O:36][CH3:37])[C:25]=1[C:54]([O:56][CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=1)=[O:55].[SH:66][C:67]1[S:71][N:70]=[N:69][CH:68]=1.[Na].O>CC(C)=O>[CH3:65][O:64][C:61]1[CH:60]=[CH:59][C:58]([CH2:57][O:56][C:54]([C:25]2[N:26]3[CH:29]([S:30][CH2:31][C:24]=2[CH2:23][S:66][C:67]2[S:71][N:70]=[N:69][CH:68]=2)[CH:28]([NH:32][C:33](=[O:52])[C:34]([C:38]2[N:39]=[C:40]([NH:43][P:44]([O:49][CH2:50][CH3:51])([O:46][CH2:47][CH3:48])=[O:45])[S:41][CH:42]=2)=[N:35][O:36][CH3:37])[C:27]3=[O:53])=[O:55])=[CH:63][CH:62]=1

Participants

6

Reactant 4

HCID 962WaterHCID 15028031(2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetic acidHCID 867458513-(Chloromethyl)-7-[[[2-[(diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxy-imino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl esterHCID 178527745HCID 178527745, compound

Product 1

HCID 765080437-[[[2-[(Diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxyimino) acetyl]amino]-8-oxo-3-[(1,2,3-thiadiazol-5-ylthio)-methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (4-methoxyphenyl)methyl EsterYield 76.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

[6R-[6-α, 7-β (Z)]]-3-(chloromethyl)-7-[[[2-[(diethoxyphosphinyl)amino]-4-thiazolyl]-(methoxy-imino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (4-methoxyphenyl)methyl ester (0.8 g) and 0.4 g sodium 5-mercapto-1,2,3-thiadiazole were stirred in 30 ml acetone plus 15 ml water for 30 minutes. The solvent was evaporated to dryness and the residue was columned on Biosil A using methylene chloride containing 0.5 to 1.0% methanol to give 687 mg of product; MS ((+)FAB) 770 (M+H); IR (KBr,cm-1) 1786, 1720.

Workup

  1. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-40e80d0a51004e75a3044e6c285b65d1
Source dataset
uspto-grants-1992_05
Patent number
US05116827

Reaction notes

Loading…