Bromomethyl acetate → HCID 12070027, 화합물

HRID 382635노트

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HRID 382635 반응식
[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]

참가 물질

4

반응물 2

HCID 68536Bromomethyl acetateHCID 23683042HCID 23683042, 화합물

생성물 1

HCID 12070027HCID 12070027, 화합물수율 19.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
-10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc649dae37e44680ac439252663b8482
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310056B1

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