Methanesulfonyl chloride → HCID 172938119, compound

HRID 376607Notes

Reaction equation

HRID 376607 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[CH2:40][CH2:39][C@H:38]([C:41]([O:43][CH3:44])=[O:42])[O:37]3)[CH2:34][S:35][C@H:30]12>CN(C)C=O.N1C=CC=CC=1>[CH3:44][O:43][C:41]([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:50]=[CH:51][C:52]([O:55][CH3:56])=[CH:53][CH:54]=2)=[O:46])[CH2:40][CH2:39]1)=[O:42]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 57294423HCID 57294423, compound

Product 1

HCID 172938119HCID 172938119, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 2-(2-aminothiazol-4-yl)-2-(Z)-methoxyiminoacetic acid (20.1mg) and N,N-diisopropylethylamine (0.0176ml) in dimethylformamide (0.3ml) was cooled to -55 to -60° C. and methanesulphonyl chloride (0.0081ml) was added. The mixture was stirred at the same temperature for 0.5h and then a solution of 4-methoxybenzyl (6R,7R)-7-amino-3-[(2S,5R)-5-methoxycarbonyltetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (41mg) in dimethylformamide (0.3ml) was added followed by pyridine (0.0073ml). The mixture was then stored at 0° C. for 1h and then at room temperature for 0.5h. 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 (31mg) isolated by column chromatography of the residue (silica gel, ethyl acetate as eluent); vmax (CHCl3) 3496, 3397, 1784, 1733 and 1684cm-1.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution
  2. washthe organic phase washed with water and brine
  3. dry with materialThe solution was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-efcfb47eabed43bdab8c168e74a09bea
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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