Dimethyl Sulfoxide → HCID 131717508, compound

HRID 1885143Notes

Reaction equation

HRID 1885143 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:59][O:60][CH3:61])[C:27]([NH:29][CH:30]2[C:57](=[O:58])[N:32]3[C:33]([C:41]([O:43][CH:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])=[C:34](/[CH:37]=[CH:38]\[CH2:39]Cl)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=[O:64]>O.[N+]([O-])([O-])=O.[Ag+]>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:59][O:60][CH3:61])[C:27]([NH:29][CH:30]2[C:57](=[O:58])[N:32]3[C:33]([C:41]([O:43][CH:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[O:42])=[C:34](/[CH:37]=[CH:38]/[CH2:39][OH:64])[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 131717509HCID 131717509, compound

Product 1

HCID 131717508HCID 131717508, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of diphenylmethyl 7-[2-(2-tritylaminothia-zol-4-yl)-2-methoxyiminoacetamido]-3-[(Z)-3-chloropropen-1-yl]-3-cephem-4-carboxylate (IIa) (715 mg, 0.825 mmol) in DMSO (9 ml) and water (2.5 ml) was added silver nitrate (700 mg) under cooling and the mixture was stirred for 6 hours at room temperature. The mixture was poured into water (50 ml) and extracted with CHCl3 (300 ml). The organic phase was washed with water and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel (Merck kieselgel 60, 20 g) by successively eluting with 0.5% MeOH/CHCl3, 1% MeOH/CHCl3 and 3% MeOH/CHCl3. The eluate was monitored by TLC and the fractions containing the desired product were combined. Evaporation under reduced pressure gave 452 mg (65% yield) of the title product as an amorphous powder.

Workup

  1. temperatureunder cooling
  2. extractionextracted with CHCl3 (300 ml)
  3. washThe organic phase was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on a column of silica gel (Merck kieselgel 60, 20 g)
  6. washby successively eluting with 0.5% MeOH/CHCl3, 1% MeOH/CHCl3 and 3% MeOH/CHCl3
  7. additionthe fractions containing the desired product
  8. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-68baa59e4c3842529adfb4dd1282f42b
Source dataset
uspto-grants-1992_09
Patent number
US05143911

Reaction notes

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