p-Bromobenzenesulfonyl chloride → Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate

HRID 5547

反応式

HRID 5547 の反応式
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:36](=[O:37])[N:14]2[C:15]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])=[C:16]([OH:19])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:40][C:41]1[CH:46]=[CH:45][C:44]([S:47](Cl)(=[O:49])=[O:48])=[CH:43][CH:42]=1>C(#N)C.[H][H]>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:36](=[O:37])[N:14]2[C:15]([C:20]([O:22][CH:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:21])=[C:16]([O:19][S:47]([C:44]3[CH:45]=[CH:46][C:41]([Br:40])=[CH:42][CH:43]=3)(=[O:49])=[O:48])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 67789034Diphenylmethyl 7-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylate

生成物 1

HCID 88424480Diphenylmethyl 7-Phenoxyacetamido-3-[(4-bromophenylsulfonyl)oxy]-3-cephem-4-carboxylate収率 54.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 178418361HCID 178418361、化合物溶媒

反応条件

温度
0 °C

実験手順

The title compound was prepared via a modification of the synthesis described in U.S. Pat. No. 3,985,737. A solution of 0.51 g (0.001 mole) of diphenylmethyl 7-phenoxyacetamido-3 -hydroxy-3-cephem- 4-carboxylate in 5 mL of acetonitrile was cooled to 0° C. under a nitrogen atmosphere. Then 0.030 g (0.001 mole) of sodium hydride (80% in mineral oil) was added resulting in hydrogen evolution. The reaction mixture was stirred at 0° C. for 5 minutes, and 0.229 g (0.009 mole) of 4-bromobenzenesulfonyl chloride was added. The cooling bath was removed, and the reaction mix stirred at room temperature for 19 hours. The reaction mixture was filtered and the filtrate carbon treated. The carbon was removed followed by the solvent to leave a foam residue. The residue was crystallized from 1-propanol to yield 0.398 g (54%) of the title compound.

後処理

  1. customThe title compound was prepared via a modification of the synthesis
  2. customThe cooling bath was removed
  3. additionthe reaction mix
  4. stirringstirred at room temperature for 19 hours
  5. filtrationThe reaction mixture was filtered
  6. additionthe filtrate carbon treated
  7. customThe carbon was removed
  8. customto leave a foam residue
  9. customThe residue was crystallized from 1-propanol

出典と根拠

ORDレコード
ord-8261f787d18e44569a78042ee44a9160
出典データセット
uspto-grants-1993_09
特許番号
US05245027

関連ノート

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