Acetic Anhydride → N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-acetoxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

HRID 6384노트

반응식

HRID 6384 반응식
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH:8]1([O:13][C:14]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[CH2:27][C:28]2[CH:51]=[CH:50][C:31]([C:32]([NH:34][S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]#[C:45][C:46]([OH:49])([CH3:48])[CH3:47])(=[O:37])=[O:36])=[O:33])=[CH:30][C:29]=2[O:52][CH3:53])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(OCC)(=O)C>[CH:8]1([O:13][C:14]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[CH:21]=[C:20]3[CH2:27][C:28]2[CH:51]=[CH:50][C:31]([C:32]([NH:34][S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[C:44]#[C:45][C:46]([O:49][C:1](=[O:3])[CH3:2])([CH3:48])[CH3:47])(=[O:36])=[O:37])=[O:33])=[CH:30][C:29]=2[O:52][CH3:53])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1

참가 물질

6

반응물 2

HCID 7918Acetic AnhydrideHCID 19793571N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

생성물 1

HCID 67884075N-[4-[5-(Cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-acetoxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

0.44 g of acetic anhydride and 0.1 g of 4-dimethylaminopyridine are added to a solution of 1.0 g of N-[4-[5-(cyclopentyloxycarbonylamino)-1-methyl-indol-3-yl-methyl]-3-methoxybenzoyl]-2-(3-hydroxy-3-methyl-but-1-yn-1-yl)-benzenesulfonamide in 6 ml of pyridine. The reaction solution is stirred for 20 hours at room temperature under argon. The reaction mixture is subsequently diluted with 100 ml of ethyl acetate. The ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time, with 50 ml of water and with 50 ml of saturated sodium chloride solution. The ethyl acetate phase is dried over magnesium sulfate and concentrated by evaporation at 20 torr and 40°. The residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1 to yield the title compound in the form of a white amorphous solid. 1H-NMR (400 MHz, DMSO-d6): 8.87 (b, 1H); 8.06 (d, d, 1H); 7.61 (m, 3H); 7.55 (d, 1H); 7.50 (d, 1H); 7.41 (d, d, 1H); 7.22 (d, 1H); 7.14 (d, d, 1H); 7.13 (d, 1H); 6.94 (s, 1H); 5.06 (m, 1H); 3.95 (s, 2H); 3.90 (s, 3H); 3.66 (s, 3H); 1.91 (s, 3H); 1.89-1.52 (m, 8H); 1.61 (s, 6H).

후처리

  1. washThe ethyl acetate phase is washed twice with 80 ml of 1N hydrochloric acid each time
  2. dry with materialThe ethyl acetate phase is dried over magnesium sulfate
  3. concentrationconcentrated by evaporation at 20 torr and 40°
  4. customThe residue is chromatographed on 50 g of silica gel (Merck, ST 60, 40-63 μm) with hexane/ethyl acetate=1/1

출처 및 근거

ORD 기록
ord-a0f180715a4a474e864218093f7ef149
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248693

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