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N-Methoxy-N,2-dimethyl-1,3-oxazole-4-carboxamide → HCID 86658082, 화합물

HRID 577894
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HRID 577894 반응식
C([Li])(CC)C.[Si:6]([O:23][CH2:24][C:25]1[C:30]([N:31]2[CH2:36][C@H:35]([CH3:37])[O:34][C@H:33]([CH3:38])[CH2:32]2)=[C:29]([F:39])[C:28]([F:40])=[CH:27][CH:26]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CON(C)[C:44]([C:46]1[N:47]=[C:48]([CH3:51])[O:49][CH:50]=1)=[O:45]>C1COCC1>[Si:6]([O:23][CH2:24][C:25]1[C:30]([N:31]2[CH2:36][C@H:35]([CH3:37])[O:34][C@H:33]([CH3:38])[CH2:32]2)=[C:29]([F:39])[C:28]([F:40])=[C:27]([C:44]([C:46]2[N:47]=[C:48]([CH3:51])[O:49][CH:50]=2)=[O:45])[CH:26]=1)([C:19]([CH3:21])([CH3:22])[CH3:20])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 24828113N-Methoxy-N,2-dimethyl-1,3-oxazole-4-carboxamideHCID 67357593(2R,6S)-4-(6-((tert-butyldiphenylsilyloxy)methyl)-2,3-difluorophenyl)-2,6-dimethylmorpholine2회HCID 178418400CID 53628100

생성물 1

HCID 86658082HCID 86658082, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

sec-Butyl lithium (1.4 M in cyclohexane, 3.2 eq) was added to a stirred solution of (2R,6S)-4-[6-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2,3-difluorophenyl]-2,6-dimethylmorpholine (Intermediate 3, 1.0 g, 2.02 mmol) in anhydrous THF (10 mL) at −78° C., and the mixture was stirred for 2 h. N-methoxy-N,2-dimethyl-1,3-oxazole-4-carboxamide (1.0 g, 6.46 mmol) in THF (5 mL) was added dropwise and stirring was continued for an additional 1 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulphate. The solvent was removed under vacuum and the residue was purified by silica gel chromatography using ethylacetate-pet. ether gradient to obtain product. Yield: 600 mg, (50%)

후처리

  1. stirringstirring
  2. waitwas continued for an additional 1 h
  3. customThe reaction mixture was quenched with saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. customThe solvent was removed under vacuum
  8. customthe residue was purified by silica gel chromatography
  9. customto obtain product

출처 및 근거

ORD 기록
ord-2a20a5a8e0de4f559f39c2313c7ef1e8
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09040528B2

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