Benzyl Bromide → HCID 22012339, compound

HRID 1533261Notes

Reaction equation

HRID 1533261 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH:19]([CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[OH:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])([OH:3])=[O:2].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:27]([O:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]([CH:19]([CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[OH:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:3])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22012438HCID 22012438, compound

Product 1

HCID 22012339HCID 22012339, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butyl 2-(2-carboxyphenylmethyl)-3-cyclohexyl-3-hydroxypropionate (200 mg) in dimethylformamide (2 ml) were added benzyl bromide (100 mg) and potassium carbonate (270 mg) successively. After being stirred for 30 minutes the mixture was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by preparative thin layer chromatography [silica gel, ethyl acetate - n-hexane (1:1)] to afford t-butyl 2-(2-benzyloxycarbonylphenylmethyl)-3-cyclohexyl-3-hydroxypropionate (108 mg).

Workup

  1. filtrationwas filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography [silica gel, ethyl acetate - n-hexane (1:1)]

Sources & evidence

ORD record
ord-e0fc3785b6564042baa7f89df9aa451b
Source dataset
uspto-grants-2001_03
Patent number
US06207686B1

Reaction notes

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