1-Bromo-3-methylbutane → HCID 68019356, compound

HRID 456263Notes

Reaction equation

HRID 456263 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[C@H:9]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:8][N:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6]1.Br[CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[OH:1][CH2:2][CH2:3][CH2:4][C@H:5]1[C@H:9]([N:10]([CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[S:11]([C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:8][N:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6]1

Participants

6

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 10796Cesium carbonateHCID 70196558HCID 70196558, compound

Product 1

HCID 68019356HCID 68019356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of tert-butyl (3R*,4S*)-3-(3-hydroxypropyl)-4-{[(4-nitrophenyl)sulfonyl]amino}pyrrolidine-1-carboxylate (0.82 g, 1.91 mmol) and 1-bromo-3-methylbutane (0.30 g, 2.0 mmol) in 8 mL DMF, Cs2CO3 (0.93 g, 2.86 mmol) was added and the mixture was stirred at 3.5 hours at 85° C. The mixture was diluted with H2O, extracted with CH2Cl2, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 1→5% MeOH in CH2Cl2 giving the title compound.

Workup

  1. additionwas added
  2. extractionextracted with CH2Cl2
  3. dry with materialthe combined organic extracts were dried with Na2SO4
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel eluting with 1→5% MeOH in CH2Cl2 giving the title compound

Sources & evidence

ORD record
ord-0ec0dfbdf5a244209c29470d862eb5fa
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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