Methanesulfonyl chloride → HCID 178500988, compound

HRID 2108210Notes

Reaction equation

HRID 2108210 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])/[C:27](O)=[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.C(N(C(C)C)CC)(C)C.CS(Cl)(=O)=O.[NH2:57][C@@H:58]1[C:84](=[O:85])[N:60]2[C:61]([C:72]([O:74][CH2:75][C:76]3[CH:81]=[CH:80][C:79]([O:82][CH3:83])=[CH:78][CH:77]=3)=[O:73])=[C:62]([S:65]/[CH:66]=[CH:67]\[C:68]([O:70][CH3:71])=[O:69])[CH2:63][S:64][C@H:59]12>CN(C)C=O.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=2[O:41][CH3:42])/[C:27]([NH:57][C@@H:58]2[C:84](=[O:85])[N:60]3[C:61]([C:72]([O:74][CH2:75][C:76]4[CH:77]=[CH:78][C:79]([O:82][CH3:83])=[CH:80][CH:81]=4)=[O:73])=[C:62]([S:65]/[CH:66]=[CH:67]\[C:68]([O:70][CH3:71])=[O:69])[CH2:63][S:64][C@H:59]23)=[O:28])[N:25]=1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 14672337HCID 14672337, compoundHCID 14672338HCID 14672338, compound

Product 1

HCID 178500988HCID 178500988, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-50 °C

Procedure

To a solution of 531 mg (0.92 mM) of 2-(2-tritylaminothiazol-4-yl)-2-[(Z)-2,4-dimethoxybenzyloxyimino]acetic acid in 10 ml of N,N-dimethylformamide was added 124 mg (0.96 mM) of diisopropylethylamine. To the cooled (-50° C.) mixture was added 105 mg (0.92 mm) of methanesulfonyl chloride, and the mixture was stirred for 30 minutes. Then, 200 mg (0.46 mM) of 4-methoxybenzyl 7β-amino-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate and 60 mg (0.46 mM) of diisopropylethylamine were added at the same temperature, and the mixture was stirred for 30 minutes. After the reaction, 30 ml of water was added, the mixture was extracted with 50 ml of ethyl acetate, and the extract was washed with 30 ml of a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel column (eluent; ethyl acetate:benzene=1:4) to give 270 mg of 4-methoxybenzyl 7β-{2-(2-tritylaminothiazol-4-yl)-2-[(Z)-2,4-dimethoxybenzyloxyimino]acetamido}-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. additionwas added
  3. extractionthe mixture was extracted with 50 ml of ethyl acetate
  4. washthe extract was washed with 30 ml of a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica gel column (eluent; ethyl acetate:benzene=1:4)

Sources & evidence

ORD record
ord-f22b181ac1054d56b8ee270c52b089f6
Source dataset
uspto-grants-1990_06
Patent number
US04937332

Reaction notes

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