Water → HCID 88645380, compound

HRID 1262751Notes

Reaction equation

HRID 1262751 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:21])=[C:15]([OH:19])[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:38](Cl)([CH3:41])(=[O:40])=[O:39].O>N1C=CC=CC=1>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[C:14]([C:20]([O:22][CH:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:21])=[C:15]([O:19][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:16][S:17](=[O:18])[C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 70411327HCID 70411327, compound

Product 1

HCID 88645380HCID 88645380, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of benzhydryl 7-phenylacetamido-3-hydroxy-3-cephem-4-carboxylate-1-oxide (40 g) in pyridine (120 ml) was added mesyl chloride (13 g) under ice-cooling. The reaction mixture was stirred at ambient temperature for an hour. The resulting suspension was poured into water (1 l). The precipitates were collected by filtration, washed with water and methanol, dried under reduced pressure to give benzhydryl 7-phenylacetamido-3-mesyloxy-3-cephem-4-carboxylate-1-oxide (37.0 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water and methanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-4adb4c602c324583842a31eacb5da361
Source dataset
uspto-grants-1984_06
Patent number
US04452851

Reaction notes

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