2,6-Dimethylbenzoic acid → 2,6-Dimethyl-benzoic acid 3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester

HRID 722742Notes

Reaction equation

HRID 722742 reaction equation
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH:8]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:9](=[O:12])[CH2:10]Br)([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:27]=1[C:28]([OH:30])=[O:29].[F-].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:17]([O:16][C:14]([NH:13][CH:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])[C:9](=[O:12])[CH2:10][O:30][C:28](=[O:29])[C:27]1[C:31]([CH3:35])=[CH:32][CH:33]=[CH:34][C:26]=1[CH3:25])=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 124392,6-Dimethylbenzoic acidHCID 522689Potassium FluorideHCID 37064953-Benzyloxycarbonylamino-5-bromo-4-oxo-pentanoic acid tert-butyl ester

Product 1

HCID 235714152,6-Dimethyl-benzoic acid 3-benzyloxycarbonylamino-4-tert-butoxycarbonyl-2-oxo-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A heterogeneous solution containing 3-benzyloxycarbonylamino-5-bromo-4-oxo-pentanoic acid tert-butyl ester, 109, (9.89 g, 24.7 mmol), 2,6-dimethyl benzoic acid (4.45 g, 29.6 mmol), and KF (3.58 g, 61.8 mmol) in 250 mL of DMF is stirred at rt for 12 h. The solution is diluted with EtOAc, washed with water, saturated NaHCO3, and brine, dried (MgSO4), and concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (hexane/EtOAc) yields 11.3 g of the desired product as a white solid.

Workup

  1. washwashed with water, saturated NaHCO3, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification of the crude material by flash chromatography on silica gel (hexane/EtOAc)

Sources & evidence

ORD record
ord-f246724e4cc742d09652060169c39a4c
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

Loading…