Benzyl Bromide → N-(2,4-dimethoxy-benzyl),N-(5-benzyloxy-2-ethoxycarbonyl-benzyl)glycine ethyl ester

HRID 2077251Notes

Reaction equation

HRID 2077251 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][N:6]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH2:7][C:8]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:9]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][N:6]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[O:29][CH3:30])[CH2:7][C:8]1[CH:13]=[C:12]([O:14][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:11]=[CH:10][C:9]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 67110496N-(2,4-dimethoxy-benzyl),N-(2-ethoxycarbonyl-5-hydroxy-benzyl)glycine ethyl ester

Product 1

HCID 67110129N-(2,4-dimethoxy-benzyl),N-(5-benzyloxy-2-ethoxycarbonyl-benzyl)glycine ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.3 g (12.3 mmol) of N-(2,4-dimethoxy-benzyl),N-(2-ethoxycarbonyl-5-hydroxy-benzyl)glycine ethyl ester, 1.8 mL (15.4 mmol) benzylbromide, and 4.4 g (13.5 mmol) cesium carbonate in 35 mL of anhydrous DMF was stirred for 18 hours. The reaction mixture was partitioned between diethyl ether and water, and the organic fraction washed with saturated aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulfate, filtered through a pad of silica gel, and concentrated under reduced pressure to 6.4 g of the title compound. MS (ESI+) 522.5 e/z (M+1)

Workup

  1. customThe reaction mixture was partitioned between diethyl ether and water
  2. washthe organic fraction washed with saturated aqueous sodium bicarbonate, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered through a pad of silica gel
  5. concentrationconcentrated under reduced pressure to 6.4 g of the title compound

Sources & evidence

ORD record
ord-487a2ea5381a497db7c2f99fd35c2b4f
Source dataset
uspto-grants-2011_04
Patent number
US07928120B2

Reaction notes

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