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Water → Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate

HRID 462594
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인쇄 미리보기

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HRID 462594 반응식
N(OC(C)(C)C)=O.[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:36]=[C:37](N)[S:38][CH:39]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(OCC)(=O)C.O>O1CCCC1>[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:36]=[CH:37][S:38][CH:39]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:14])([CH3:11])([CH3:9])[CH3:10]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10906Tert-Butyl nitriteHCID 53827226Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetate

생성물 1

HCID 54223791Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate수율 45.5%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A solution of t-butyl nitrite (1.7 g) in tetrahydrofuran (10 ml) was dropwise added to a solution of benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetate (syn isomer) (5 g) in tetrahydrofuran (50 ml) at 50° to 53° C. under stirring and the mixture was stirred at the same temperature at 25 minutes. The reaction mixture was poured into a mixture of ethyl acetate and water and the organic layer was separated. The organic layer was washed with brine and dried over magnesium sulfate. The solution was evaporated and the residue was subjected to column chlomatography on silica gel. The elution was carried out with a mixture of benzene and ethyl acetate (19:1) and the eluates containing the object compound were evaporated to give benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate (syn isomer) (2.2 g).

후처리

  1. stirringthe mixture was stirred at the same temperature at 25 minutes
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated
  6. washThe elution
  7. additionwas carried out with a mixture of benzene and ethyl acetate (19:1)
  8. additionthe eluates containing the object compound
  9. customwere evaporated

출처 및 근거

ORD 기록
ord-e221332a3a5444e3aac1a75f1113c757
출처 데이터셋
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04515788

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