Methanesulfonyl chloride → HCID 178502810, compound

HRID 1421828Notes

Reaction equation

HRID 1421828 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([OH:10])=O)[N:6]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[NH2:28][C@@H:29]1[C:57](=[O:58])[N:31]2[C:32]([C:45]([O:47][CH2:48][C:49]3[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=3)=[O:46])=[C:33]([C@@H:36]3[C:40](=[C:41]=[O:42])[CH2:39][C@H:38]([O:43][CH3:44])[O:37]3)[CH2:34][S:35][C@H:30]12>CN(C)C=O.N1C=CC=CC=1>[CH3:44][O:43][C@@H:38]1[O:37][C@H:36]([C:33]2[CH2:34][S:35][C@@H:30]3[C@H:29]([NH:28][C:8](=[O:10])/[C:7](/[C:5]4[N:6]=[C:2]([NH2:1])[S:3][CH:4]=4)=[N:11]\[O:12][CH3:13])[C:57](=[O:58])[N:31]3[C:32]=2[C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)=[O:46])[C:40](=[C:41]=[O:42])[CH2:39]1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 131721861HCID 131721861, compound

Product 1

HCID 178502810HCID 178502810, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (20.1 mg) and N,N-diisopropylethylamine (0.0176 ml) in dimethylformamide (0.3 ml) was cooled to -55 to -60° C. and methanesulphonyl chloride (0.0081 ml) was added. The mixture was stirred at the same temperature for 0.5 h and then a solution of 4-methoxybenzyl (6R,7R)-7-amino-3-[(2S,5R)-5-methoxy-carbonyltetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (41 mg) in dimethylformamide (0.3 ml) was added followed by pyridine (0.0073 ml). The mixture was then stored at 0° C. for 1 h and then at room temperature for 0.5 h. The reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution and the organic phase washed with water and brine. The solution was dried over magnesium sulphate and evaporated, and the title compound (31 mg) isolated by column chromatography of the residue (silica gel, ethyl acetate as eluent); νmax (CHCl3) 3496, 3397, 1784, 1733 and 1684 cm-1.

Workup

  1. waitThe mixture was then stored at 0° C. for 1 h
  2. waitat room temperature for 0.5 h
  3. customThe reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution
  4. washthe organic phase washed with water and brine
  5. dry with materialThe solution was dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-4e0849cbf0a84c4486bd2e34a1318a31
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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