Allyl bromide → HCID 67439909, compound

HRID 1664221Notes

Reaction equation

HRID 1664221 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:5]=1.[CH2:28](Br)[CH:29]=[CH2:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[C:6]([N:16]([CH2:30][CH:29]=[CH2:28])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH:5]=1

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 67438703HCID 67438703, compound

Product 1

HCID 67439909HCID 67439909, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 3.69 g (8.1 mmol) 3-benzyloxycarbonylamino-5-(2-oxo-pyrrolidin-1-yl)-benzoic acid methyl ester, 1.37 ml (16.2 mmol) allyl bromide, 2.24 g (16.2 mmol) potassium carbonate in 8 ml DMF is stirred at 50° C. for 4 h. The mixture is diluted with water and extracted with EtOAc. The organic phase is washed with water and dried over sodium sulfate. The product is purified by chromatography on silica gel (EtOAc/hexanes 1:4, 1:2, 1:1, 2:1). The title compound is isolated as a yellow resin.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe product is purified by chromatography on silica gel (EtOAc/hexanes 1:4, 1:2, 1:1, 2:1)

Sources & evidence

ORD record
ord-a14a8cfbe89144aea7f5b384b93304e7
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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