Tetrahydrofuran → HCID 14257300, 화합물

HRID 622588노트

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HRID 622588 반응식
[CH3:1][S:2]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)=O.[O:30]1[CH2:34]CC[CH2:31]1.[OH-:35].[Na+]>CO>[CH3:31][O:30][C:34]([CH2:1][S:2][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:35]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12590460(3R,4R)-4-(Methanesulfonyl)-3-[(triphenylmethyl)amino]azetidin-2-one

생성물 1

HCID 14257300HCID 14257300, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 10 g of (3R,4R)-4-methylsulfonyl-3-tritylamino-2-azetidinone in 250 ml of methanol is added 100 ml of tetrahydrofuran, followed by addition of 3.45 g of methyl thioglycollate and 32.5 ml of 1N sodium hydroxide under ice-cooling, and the mixture is stirred at room temperature for 30 minutes. The solvent is then distilled off under reduced pressure and 100 ml of ethyl acetate is added. The ethyl acetate layer is separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue is purified by silica gel column chromatography using n-hexane-ethyl acetate (3:2). The earlier eluate fractions are combined and concentrated under reduced pressure to give 4.35 g of (3R,4R)-4-[[(methoxycarbonyl)methyl]thio]-3-tritylamino-2-azetidinone.

후처리

  1. temperaturecooling
  2. distillationThe solvent is then distilled off under reduced pressure and 100 ml of ethyl acetate
  3. additionis added
  4. customThe ethyl acetate layer is separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b620e0c17b084c2092108173af991335
출처 데이터셋
uspto-grants-1988_09
특허 번호
US04771045

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