Diisopropylethylamine → Diphenylmethyl 7beta-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate

HRID 992679Notes

Reaction equation

HRID 992679 reaction equation
[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:8](OS(C)(=O)=O)[CH2:9][S:10][C@H:5]12)=[O:2].[SH:34][CH2:35][C:36]1[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH:1]([NH:3][C@@H:4]1[C:32](=[O:33])[N:6]2[C:7]([C:16]([O:18][CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:17])=[C:8]([S:34][CH2:35][C:36]3[CH:41]=[CH:40][N:39]=[CH:38][CH:37]=3)[CH2:9][S:10][C@H:5]12)=[O:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10863874Diphenylmethyl 7beta-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylateHCID 13092602Pyridin-4-ylmethanethiol

Product 1

HCID 88157711Diphenylmethyl 7beta-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylateYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate (14.66 g, 30 m mol) in DMF (103 ml) was added 4-(mercaptomethyl)pyridine (4.13 g, 33 m mol) at −20° C., followed by dropwise addition of N,N-diisopropylethylamine (3.88 g, 30 m mol). The mixture was stirred at the same temperature for 1.9 hours and poured into ice water (500 ml). The resulting precipitates were collected by filtration and washed with water. The powder was dissolved in THF, and ethyl acetate and water were added respective. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give diphenylmethyl 7β-formamido-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (13.73 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. dissolutionThe powder was dissolved in THF
  5. additionethyl acetate and water were added respective
  6. washThe separated organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cceead8440d241e1be5be0bda81c26b1
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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