1-Bromo-3-methylbutane → HCID 70202042, compound

HRID 456252Notes

Reaction equation

HRID 456252 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:10]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34](Br)[CH2:35][CH:36]([CH3:38])[CH3:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:12][C@@H:11]([N:13]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C@H:10]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:30])([CH3:32])[CH3:31])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 78911-Bromo-3-methylbutaneHCID 11430Potassium CarbonateHCID 70201301HCID 70201301, compound

Product 1

HCID 70202042HCID 70202042, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tert-butyl [(3R,4R)-1-benzyl-4-{[(4-nitrophenyl)sulfonyl]amino}pyrrolidin-3-yl]carbamate (4.76 g, 10 mmol), isoamyl bromide (1.2 eq), and K2CO3 (2.76 g, 20 mmol) in 50 mL of DMF was stirred overnight at 50° C. The mixture was diluted with H2O, extracted with EtOAc, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 5→20% EtOAc in hexane to give the title product.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe combined organic extracts were dried with Na2SO4
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel eluting with 5→20% EtOAc in hexane

Sources & evidence

ORD record
ord-bb8f42812adf4bd1a996c926163abf63
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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