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

HRID 386721Notes

Reaction equation

HRID 386721 reaction equation
C([O:8][C:9](=[O:31])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:24](=[O:30])[N:25]([CH2:27][CH2:28][OH:29])[CH3:26])[C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1)C1C=CC=CC=1>CO.[Pd]>[OH:29][CH2:28][CH2:27][N:25]([CH3:26])[C:24]([CH:19]([C:20]([O:22][CH3:23])=[O:21])[O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][C:9]([OH:31])=[O:8])=[CH:13][CH:14]=1)=[O:30]

Participants

4

Reactant 1

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

Product 1

HCID 667975743-(4-{[(2-Hydroxy-ethyl)-methyl-carbamoyl]-methoxycarbonylmethoxy}-phenyl)-propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-(4-{[(2-hydroxy-ethyl)-methyl-carbamoyl]-methoxycarbonylmethoxy}-phenyl)-propionic acid benzyl ester (step 3) (0.44 g, 1.02 mmol) in MeOH (20 ml) was treated with palladium on activated carbon (10% wt, 50 mg, 0.047 mmol) and stirred under an atmosphere of hydrogen for 20 h at RT. The reaction mixture was filtered through Celite® (filter material) and washed through with EtOAc. The filtrate was concentrated in vacuo and purification of the crude product by chromatography on silica eluting with 0-10% MeOH in DCM afforded the title compound; LC-MS: 340.2 [M+H]+

Workup

  1. filtrationThe reaction mixture was filtered through Celite® (filter material)
  2. washwashed through with EtOAc
  3. concentrationThe filtrate was concentrated in vacuo and purification of the crude product by chromatography on silica eluting with 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-7a364718f9874d6fb53feb941d5af803
Source dataset
uspto-grants-2013_02
Patent number
US08372845B2

Reaction notes

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