Sodium Bicarbonate → {1-Benzyl-2-hydroxy-3-[isobutyl-(2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-amino]-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

HRID 1158257노트

반응식

HRID 1158257 반응식
[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]([OH:20])[CH2:14][NH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:2]1.C(=O)(O)[O-].[Na+].[O:34]=[C:35]1[CH2:43][C:42]2[C:37](=[CH:38][CH:39]=[C:40]([S:44](Cl)(=[O:46])=[O:45])[CH:41]=2)[NH:36]1>C(Cl)Cl.C(OCC)(=O)C>[O:1]1[CH:5]2[O:6][CH2:7][CH2:8][CH:4]2[CH:3]([O:9][C:10](=[O:28])[NH:11][CH:12]([CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:13]([OH:20])[CH2:14][N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:44]([C:40]2[CH:41]=[C:42]3[C:37](=[CH:38][CH:39]=2)[NH:36][C:35](=[O:34])[CH2:43]3)(=[O:45])=[O:46])[CH2:2]1

참가 물질

6

반응물 3

HCID 516892Sodium Bicarbonate2회HCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chlorideHCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

생성물 1

HCID 58612411{1-Benzyl-2-hydroxy-3-[isobutyl-(2-oxo-2,3-dihydro-1H-indole-5-sulfonyl)-amino]-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester수율 90%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (1-benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (59 mg, 0.15 mmol) in CH2Cl2 (1.6 ml) was added saturated aqueous sodium bicarbonate (0.4 ml), solid sodium bicarbonate (16 mg, 0.19 mmol), and then 2-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride 14 (42 mg, 0.18 mmol). The mixture was stirred overnight, diluted with ethyl acetate, washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to provide the title product as a white solid, (79 mg, 90%). TLC: Rf 0.33 (Ethyl acetate). MS m/z 588 (MH)+. 1H NMR (CDCl3) is consistent with the structure.

후처리

  1. washwashed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9f74c7cdf5a34a7086ebad7cc362527b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807845B2

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