Iodine → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{5-[3-(2-ethylbutyl)cyclobutyl]-4-iodoisoxazol-3-yl}valerate

HRID 1912096노트

반응식

HRID 1912096 반응식
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30](=[N:43][O:44]C)[C:31]#[C:32][CH:33]1[CH2:36][CH:35]([CH2:37][CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH2:34]1)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([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(#N)C.[I:49]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30]1[C:31]([I:49])=[C:32]([CH:33]2[CH2:36][CH:35]([CH2:37][CH:38]([CH2:41][CH3:42])[CH2:39][CH3:40])[CH2:34]2)[O:44][N:43]=1)[CH2:22][C:23]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:24])([C:14]([CH3:17])([CH3:15])[CH3:16])([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

참가 물질

6

반응물 4

HCID 807IodineHCID 6342AcetonitrileHCID 24477Sodium Thiosulfate2회HCID 86675053tert-Butyl 3-[2-(tert-butyldiphenylsilanyloxy)ethyl]-6-[3-(2-ethylbutyl)cyclobutyl]-4-methoxyimino-5-hexynoate

생성물 1

HCID 71127336tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-{5-[3-(2-ethylbutyl)cyclobutyl]-4-iodoisoxazol-3-yl}valerate수율 80.4%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl 3-[2-(tert-butyldiphenylsilanyloxy)ethyl]-6-[3-(2-ethylbutyl)cyclobutyl]-4-methoxyimino-5-hexynoate (7.50 g) and acetonitrile (60 mL) were mixed. To the mixture was added iodine (7.54 g) was added at ice temperature. The mixture was stirred for 4.5 hr, and then to the mixture were added aqueous 5 w/v % sodium thiosulfate (50 mL), ethyl acetate (200 mL) and aqueous 5 w/v % sodium thiosulfate (75 mL, 150 mL) at ice temperature. The aqueous layer was removed, and the organic layer was washed with saturated aqueous sodium bicarbonate/brine=1/1 (100 mL) and brine (50 mL), then dried over sodium sulfate. The sodium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified twice by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/50→1/40→1/20) to give the title compound (7.1 g).

후처리

  1. additionwas added at ice temperature
  2. customThe aqueous layer was removed
  3. washthe organic layer was washed with saturated aqueous sodium bicarbonate/brine=1/1 (100 mL) and brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationThe sodium sulfate was filtered off
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified twice by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/50→1/40→1/20)

출처 및 근거

ORD 기록
ord-2a7c132093984180a87ae511a7ffa10d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604069B2

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