Tetrachlorocatechol → HCID 54215510, 화합물

HRID 1871729

반응식

HRID 1871729 반응식
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].[Cl:7][C:8]1[C:9]([Cl:18])=[C:10]([Cl:17])[C:11]([Cl:16])=[C:12]([OH:15])[C:13]=1[OH:14].[C:19]([O:23][C:24]([CH:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31](=[O:34])[CH2:32]Br)=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[C:2]([O:5][C:24]([C@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31](=[O:34])[CH2:32][O:14][C:13]1[C:8]([Cl:7])=[C:9]([Cl:18])[C:10]([Cl:17])=[C:11]([Cl:16])[C:12]=1[O:15][CH2:32][C:31]([N:27]1[CH2:28][CH2:29][CH2:30][C@@H:26]1[C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:25])=[O:34])=[O:23])([CH3:4])([CH3:3])[CH3:1]

참가 물질

5

반응물 3

HCID 14537TetrachlorocatecholHCID 23665647Potassium tert-butoxideHCID 70037232HCID 70037232, 화합물

생성물 1

HCID 54215510HCID 54215510, 화합물수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To a solution of 185 mg (1.65 mmol) potassium tert-butylate in 1 ml dimethylformamide at room temperature was added dropwise a solution of 186 mg (0.75 mmol) tetrachlorocatechol in 1 ml dimethylformamide. Stirring was continued for 2-3 min and a solution of 438 mg (1.50 mmol) (R)-(1) -bromoacetyl-pyrrolidine-2-carboxylic acid tert-butyl ester in 2 ml dimethylformamide was added within 1-2 min. The reaction mixture was stirred for additional 4 h at room temperature. The solvent was removed in vacuo and the residue purified by flash-chromatography to yield 229 mg (45%) of the title compound as a white foam. MS m/e (%): 671 (M+H+, 100), 615 (19), 559 (14).

후처리

  1. stirringThe reaction mixture was stirred for additional 4 h at room temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by flash-chromatography

출처 및 근거

ORD 기록
ord-8440744a0f3447d3b46c4f0f0cb923c7
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06103910

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