Tetrahydrofuran → tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-nitrophenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

HRID 29191

반응식

HRID 29191 반응식
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@H:9]([OH:18])[CH2:10][NH:11]OC1CCCC1)([CH3:4])([CH3:3])[CH3:2].[N+:27]([C:30]1[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28].[CH2:40]1[CH2:44][O:43][CH2:42][CH2:41]1.[CH:45](N(C(C)C)CC)(C)C>CCOC(C)=O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C@@H:9]([OH:18])[CH:10]([NH:11][S:36]([C:32]1[CH:33]=[CH:34][CH:35]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=1)(=[O:38])=[O:37])[O:43][CH:44]1[CH2:40][CH2:41][CH2:42][CH2:45]1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 84763-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 21356391tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate

생성물 1

HCID 86585039tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)[(3-nitrophenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate (0.52 g, 1.4 mmol) was combined with 3-nitrobenzenesulfonyl chloride (0.47 g, 2.1 mmol) in freshly distilled THF (5 ml). Diisopropylethylamine (0.74 ml, 4.3 mmol) was added and the reaction was stirred at room temperature overnight. Reaction mixture was diluted in EtOAc and washed with 0.5 N KHSO4, and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purication by flash chromatography (1:4/EtOAc/Hex gradient to 1:3, to 1:2, to 1:1 and then to 2:1). Recovered 0.44 g (56%) of the product as a white foam. Rf=0.45 (2:1 EtOAc/Hex), 1H NMR (CDCl3) 8.67 (1H, s), 8.49 (1H, d), 8.08 (1H, d), 7.77 (1H, t), 7.36-7.17 (5H, m), 4.88 (1H,m), 4.62 (1H,b), 3.88-3.71 (2H,m), 3.41 (1H,b), 3.07 (1H,b), 2.98-2.79 (3H,m), 1.92-1.75 (4H,m), 1.73-1.52 (4H,m), 1.45 (9H,s).

후처리

  1. customReaction mixture
  2. washwashed with 0.5 N KHSO4, and brine
  3. dry with materialOrganic phase was dried with MgSO4 and solvent
  4. customwas removed in vacuo
  5. customRecovered 0.44 g (56%) of the product as a white foam

출처 및 근거

ORD 기록
ord-3eba50de559c4b22b5d625c8be8ad67c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

연결된 노트

불러오는 중…