Methanesulfonyl chloride → HCID 178502809, compound

HRID 973865Notes

Reaction equation

HRID 973865 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(C(C)C)CC)(C)C.CS(Cl)(=O)=O.[NH2:28][C@@H:29]1[C:63](=[O:64])[N:31]2[C:32]([C:47]([O:49][CH:50]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])=[C:33](/[CH:36]=[C:37]3/[O:38][C:39]([C:41]4[C:46]/3=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:40])[CH2:34][S:35][C@H:30]12>CN(C=O)C.ClCCl.N1C=CC=CC=1>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][CH3:13])/[C:8]([NH:28][C@@H:29]2[C:63](=[O:64])[N:31]3[C:32]([C:47]([O:49][CH:50]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[C:51]4[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=4)=[O:48])=[C:33](/[CH:36]=[C:37]4/[O:38][C:39]([C:41]5[C:46]/4=[CH:45][CH:44]=[CH:43][CH:42]=5)=[O:40])[CH2:34][S:35][C@H:30]23)=[O:10])[N:6]=1

Participants

8

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 67923927HCID 67923927, compound

Product 1

HCID 178502809HCID 178502809, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(2-Aminothiazol-4-yl)-2-Z-methoxyiminoacetic acid (0.018 g) in dry DMF (2 mls) under argon was cooled to -50° C. and treated successively with diisopropylethylamine (0.091 mls) and methanesulphonyl chloride (0.04 mls) for 1 h. A solution of diphenylmethyl 7β-amino-3-(E-phthalidylidenemethyl)ceph-3-em-4-carboxylate (0.222 g) in dichloromethane (3 mls) and pyridine (0.035 mls) was added to the activated intermediate at -50° C. and the solution then allowed to warm slowly to room temperature. The solution was diluted with dichloromethane and washed with water and brine, and then dried. After removal of solvent, the crude product was purified by flash chromatography on silica gel, eluting with ethyl acetate. The title compound was obtained as a yellow amorphous solid, (0.051 g), 17%), νmax (CH2Cl2) 1780(s), 1720(w), 1680(w), 1600(w), 1520(w br) and 1365cm-1 ; δH (CDCl3) 3.59 (2H,ABq,J18.6Hz), 4.09 (3H,s), 5.28(1H,d,J4.9Hz), 5.48 (2H,br.s, exch.), 6.20 (1H,dd,J4.9,8.9Hz; collapses to d on D2O shake, J4.9Hz), 6.42 (1H,s), 6.83 (1H,s), 6.88(1H,s), 7.22 (10 H,m), 7.4-7.6 (3H,m), 7.86 (1H,m) and 7.98 (1H,d,J8.9Hz, exch.); [mass spectrum: +ve ion (3-NOBA, Na+) MNa+, 716].

Workup

  1. washwashed with water and brine
  2. customdried
  3. customAfter removal of solvent
  4. customthe crude product was purified by flash chromatography on silica gel
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e91621a9489247ca8ee2e05b0643aac2
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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