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

HRID 29192

Reaction equation

HRID 29192 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-80392b89ee484fe3b98243eddcccd240
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Linked notes

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