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

HRID 29191

反応式

HRID 29191 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3eba50de559c4b22b5d625c8be8ad67c
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

関連ノート

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