Methanesulfonyl chloride → HCID 9915982, compound

HRID 376576Notes

Reaction equation

HRID 376576 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:52](=[O:53])[N:31]2[C:32]([C:41]([O:43][CH2:44][O:45][C:46](=[O:51])[C:47]([CH3:50])([CH3:49])[CH3:48])=[O:42])=[C:33]([C@@H:36]3[CH2:40][CH2:39][CH2:38][O:37]3)[CH2:34][S:35][C@H:30]12>CN(C=O)C>[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:52](=[O:53])[N:31]3[C:32]([C:41]([O:43][CH2:44][O:45][C:46](=[O:51])[C:47]([CH3:49])([CH3:50])[CH3:48])=[O:42])=[C:33]([C@@H:36]4[CH2:40][CH2:39][CH2:38][O:37]4)[CH2:34][S:35][C@H:30]23)=[O:10])[N:6]=1

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine2×HCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 53848400HCID 53848400, compound

Product 1

HCID 9915982HCID 9915982, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-50 °C

Procedure

A solution of (Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetic acid (0.108g, 0.537mmol) in DMF (2ml) was cooled to -50° C. N,N-Diisopropylethylamine (0.103ml, 0.59mmol) followed by methanesulphonyl chloride (0.046ml, 0.59mmol) were added and the mixture was stirred at -50° C. for 30 min. A further quantity of N,N-diisopropylethylamine (0.086ml, 0.493mmol) was added and this mixture was added to a pre-cooled solution of pivaloyloxymethyl (6R,7R)-7-amino-3-[(S)-tetrahydrofuran-2-yl]ceph-3-em-4-carboxylate (0.185g, 0.482mmol) in DMF (2ml) at 0° C. The resulting mixture was stirred at 0° C. for 40 min., then it was partitioned between ethyl acetate and water. The organic phase was washed with water, brine, dried (MgSO4) and evaporated. The residue was purified by flash chromatography, then triturated with ether to give the title compound (0.193g, 71%) as a white solid. The spectral data was identical with that obtained for Example 8.

Workup

  1. additionwere added
  2. stirringThe resulting mixture was stirred at 0° C. for 40 min.
  3. customit was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. customtriturated with ether

Sources & evidence

ORD record
ord-25ddea48074d45b889a8ee2cfa6e9c24
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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