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

HRID 29192

반응식

HRID 29192 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].[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]

참가 물질

6

반응물 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

생성물 1

HCID 86585040tert-Butyl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy) (2-[(methoxycarbonyl)amino]benzimidazol-5-ylsulfonyl)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 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-80392b89ee484fe3b98243eddcccd240
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07419967B2

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