Sodium Bicarbonate → 3-(4-{[(2-Hydroxy-ethyl)-methyl-carbamoyl]-methoxycarbonylmethoxy}-phenyl)-propionic acid benzyl ester

HRID 386720Notes

Reaction equation

HRID 386720 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC[C:26]([N:28]([CH2:30][CH2:31][OH:32])[CH3:29])=[O:27].[C:33](=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:23])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:18][CH:19]([C:26](=[O:27])[N:28]([CH2:30][CH2:31][OH:32])[CH3:29])[C:20]([O:22][CH3:33])=[O:21])=[CH:16][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 131886572-chloro-N-(2-hydroxyethyl)-N-methylacetamideHCID 667975903-(4-Carboxymethoxy-phenyl)-propionic acid benzyl ester

Product 1

HCID 667977153-(4-{[(2-Hydroxy-ethyl)-methyl-carbamoyl]-methoxycarbonylmethoxy}-phenyl)-propionic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture comprising 3-(4-carboxymethoxy-phenyl)-propionic acid benzyl ester (Step 2) (0.65 g, 1.93 mmol) and 2-chloro-N-(2-hydroxy-ethyl)-N-methyl-acetamide (0.35 g, 2.31 mmol) in DMF (10 ml) and sodium hydrogen carbonate (2.5 equivalents) was stirred at RT for 2 days and concentrated in vacuo. The crude residue was purified by chromatography on silica eluting with 0-5% MeOH in DCM to afford the title product as a viscous oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude residue was purified by chromatography on silica eluting with 0-5% MeOH in DCM

Sources & evidence

ORD record
ord-2e6ea78aa0314c179df4919b54a8336a
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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