1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose → 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester

HRID 1827005

반응식

HRID 1827005 반응식
[CH3:1][C:2]1([CH3:18])[O:10][C@H:9]2[C@H:4]([C@@H:5]([CH2:16][OH:17])[O:6][C@@H:7]3[O:13][C:12]([CH3:15])([CH3:14])[O:11][C@@H:8]32)[O:3]1.[CH3:19][C:20]1[CH:24]=[C:23]([CH3:25])[NH:22][C:21]=1/[CH:26]=[C:27]1\[C:28](=[O:39])[N:29]([C:36](Cl)=[O:37])[C:30]2[C:35]\1=[CH:34][CH:33]=[CH:32][CH:31]=2>N1C=CC=CC=1.C1COCC1>[CH3:15][C:12]1([CH3:14])[O:13][C@H:7]2[O:6][CH:5]([CH2:16][O:17][C:36]([N:29]3[C:30]4[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=4)/[C:27](=[CH:26]/[C:21]4[NH:22][C:23]([CH3:25])=[CH:24][C:20]=4[CH3:19])/[C:28]3=[O:39])=[O:37])[C@@H:4]3[O:3][C:2]([CH3:18])([CH3:1])[O:10][C@@H:9]3[C@H:8]2[O:11]1

참가 물질

5

반응물 2

HCID 27236291,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranoseHCID 879046953-[1-(3,5-Dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride

생성물 1

HCID 1317245993-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR, 5aS, 8aS, 8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethyl ester수율 65%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1,2,3,4-di-O-isopropylidene-D-galactopyranose (650 mg, 2.5 mmol) in 1.0 mL of pyridine and 2.0 mL of THF was added a suspension of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carbonyl chloride (150 mg, 0.5 mmol) at 0° C. The reaction mixture was then gradually warmed to room temperature, stirred for 4 h, and concentrated. The residue was triturated with water and washed with ether to give 170 mg (65%) of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid (3aR,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4′,5′-d]pyran-5-ylmethyl ester.

후처리

  1. concentrationconcentrated
  2. customThe residue was triturated with water
  3. washwashed with ether

출처 및 근거

ORD 기록
ord-c267807db604480a9f586d346fb4366b
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053114B2

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