proline dl-form → 5-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561388

반응식

HRID 561388 반응식
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.N1CCCC1C(O)=O.[Br:19][C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1.[CH3:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2>C(#N)C>[Br:19][C:20]1[S:21][C:22]([CH:25]([C:35]2[C:34]3[C:38](=[C:30]([CH2:29][S:28][CH3:27])[CH:31]=[CH:32][CH:33]=3)[NH:37][CH:36]=2)[CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:23][N:24]=1

참가 물질

6

반응물 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

생성물 1

HCID 583922715-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

1.02 g (7.08 mmol) of Meldrum's acid, 0.04 g (0.34 mmol) of D,L-proline and 1.36 g (7.08 mmol) of 2-bromo-5-formylthiazole were successively added to a solution of 1.30 g (6.75 mmol) of the compound from Example 8A in 50 ml of acetonitrile. The reaction mixture was stirred at RT overnight and then the solvent was removed in vacuo. Purification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) resulted in 3.58 g (81% purity, 87% of theory) of the title compound.

후처리

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

출처 및 근거

ORD 기록
ord-f7633072c4254390973e72a6a89551ba
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063234B2

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