1-[4-(3-t-Butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidine → 3-Acetylthio-1-[4-(3-t-butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine

HRID 891818노트

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HRID 891818 반응식
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]([C:25]2[N:26]=[C:27]([N:30]3[CH2:33][CH:32](OS(C)(=O)=O)[CH2:31]3)[O:28][CH:29]=2)=[O:24])[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:39]([O-:42])(=[S:41])[CH3:40].[K+]>CN(C)C=O>[C:39]([S:41][CH:32]1[CH2:33][N:30]([C:27]2[O:28][CH:29]=[C:25]([C:23]([N:21]3[CH2:20][CH:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:22]3)=[O:24])[N:26]=2)[CH2:31]1)(=[O:42])[CH3:40]

참가 물질

4

반응물 2

HCID 222428271-[4-(3-t-Butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidineHCID 23670855Potassium ethanethioate

생성물 1

HCID 222429903-Acetylthio-1-[4-(3-t-butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine수율 57.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of 1-[4-(3-t-butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]-3-methanesulfonyloxyazetidine (1.56 g, 2.81 mmol) (obtained as described in Reference Example 74(2)) in dimethylformamide (80 ml) was added potassium thioacetate (1.92 g, 16.8 mmol) at room temperature and the mixture was stirred in an oil bath (80° C.) for 7.5 hours. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1→1:1) as the eluant to afford 3-acetylthio-1-[4-(3-t-butyldiphenylsilyloxyazetidine-1-carbonyl)-1,3-oxazol-2-yl]azetidine (863 mg, yield 57%) as a pale brown solid.

후처리

  1. customat room temperature
  2. customthe completion of the reaction
  3. customthe mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-6defc27ef4e947e5840960902406af16
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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