Dimethylformamide → tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy) (2-[(methoxycarbonyl)amino]benzimidazol-5-ylsulfonyl)amino-2-hydroxypropyl)carbamate

HRID 29192

反応式

HRID 29192 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].[CH3:27][O:28][C:29]([NH:31][C:32]1[NH:33][C:34]2[CH:40]=[C:39]([S:41](Cl)(=[O:43])=[O:42])[CH:38]=[CH:37][C:35]=2[N:36]=1)=[O:30].[CH:45]([C:48]([CH:53]([CH3:55])C)(NCC)C)([CH3:47])C.CN(C=[O:60])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:41]([C:39]1[CH:38]=[CH:37][C:35]2[N:36]=[C:32]([NH:31][C:29]([O:28][CH3:27])=[O:30])[NH:33][C:34]=2[CH:40]=1)(=[O:43])=[O:42])[O:60][CH:45]1[CH2:48][CH2:53][CH2:55][CH2:47]1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 15124047Methyl N-[6-(chlorosulfonyl)-1H-benzimidazol-2-yl]carbamateHCID 21356391tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamateHCID 21936557Diisopropyldiethylamine

生成物 1

HCID 86585040tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy) (2-[(methoxycarbonyl)amino]benzimidazol-5-ylsulfonyl)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 (step 1, Example 54), (0.75 g, 2.1 mmol) was combined with 2-(methoxycarbonyl)amino benzimidazol-5-ylsulfonyl chloride (0.89 g, 3.1 mmol) in anhydrous DMF (15 ml) under a N2 atmosphere. Diisopropylethylethyl amine (1.08 ml, 6.2 mmol) was added and the reaction was stirred at room temperature for 24 hours. The reaction mixture was diluted in EtOAc and washed with sat. NaHCO3, 0.5N KHSO4 and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by flash chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% to 3% to 4%). Recovered 0.79 g (62%) of product as a white foam. Rf=0.08 (3% MeOH/CH2Cl2). HPLC tR=10.47 min (C18 column). LRMS (M+H)+ 618.2.

後処理

  1. washwashed with sat. NaHCO3, 0.5N KHSO4 and brine
  2. dry with materialOrganic phase was dried with MgSO4 and solvent
  3. customwas removed in vacuo
  4. customPurification by flash chromatography (CH2Cl2 to 1% MeOH in CH2Cl2 to 2% to 3% to 4%)
  5. customRecovered 0.79 g (62%) of product as a white foam

出典と根拠

ORDレコード
ord-80392b89ee484fe3b98243eddcccd240
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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