Bromomethyl acetate → HCID 12070027、化合物

HRID 382635ノート

反応式

HRID 382635 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O-:21])=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+].[C:25]([O:28][CH2:29]Br)(=[O:27])[CH3:26]>CN(C=O)C>[OH:1][C@@H:2]([C@H:4]1[C:22](=[O:23])[N:6]2[C:7]([C:19]([O:21][CH2:29][O:28][C:25](=[O:27])[CH3:26])=[O:20])=[C:8]([C:11]3[S:15][C:14]4=[CH:16][N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

参加物

4

反応物 2

HCID 68536Bromomethyl acetateHCID 23683042HCID 23683042、化合物

生成物 1

HCID 12070027HCID 12070027、化合物収率 19.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-10 °C

実験手順

To a solution of 49 mg of sodium (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-(imidazo[5,1-b]thiazol-2-yl)-1-methyl-1-carbapen-2-em-3-carboxylate in 1 ml of DMF was added 32 mg of acetoxymethyl bromide under the atmosphere of argon at −20° C., and the mixture was stirred for 3 hours during which the temperature was raised up to −10° C. The reaction mixture was extracted twice with 20 ml of ethyl acetate, and the organic layer was washed twice with 10 ml of semi-saturated aqueous saline, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to a volume of 2 ml. The residue thus obtained was purified by column chromatography on silica gel (chloroform:methanol=9:1) and on Sephadex LH-20 (dichloromethane:methanol=1:1) in this sequence to give 11 mg of the title compound.

後処理

  1. extractionThe reaction mixture was extracted twice with 20 ml of ethyl acetate
  2. washthe organic layer was washed twice with 10 ml of semi-saturated aqueous saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure to a volume of 2 ml
  6. customThe residue thus obtained
  7. customwas purified by column chromatography on silica gel (chloroform:methanol=9:1) and on Sephadex

出典と根拠

ORDレコード
ord-bc649dae37e44680ac439252663b8482
出典データセット
uspto-grants-2001_10
特許番号
US06310056B1

反応ノート

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