methyl (E)-3-(2-benzyloxy-4-methoxyphenyl)-2-(tert-butoxycarbonyl-amino)acrylate → Methyl 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxyphenyl)-propanoate

HRID 540412Notes

Reaction equation

HRID 540412 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1/[CH:17]=[C:18](/[NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])\[C:19]([O:21][CH3:22])=[O:20])C1C=CC=CC=1>CO.[Pd]>[C:27]([O:26][C:24]([NH:23][CH:18]([CH2:17][C:10]1[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:9]=1[OH:8])[C:19]([O:21][CH3:22])=[O:20])=[O:25])([CH3:29])([CH3:30])[CH3:28]

Participants

4

Reactant 1

HCID 66988070methyl (E)-3-(2-benzyloxy-4-methoxyphenyl)-2-(tert-butoxycarbonyl-amino)acrylate

Product 1

HCID 397418Methyl 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxyphenyl)-propanoateYield 74.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

350 mg of palladium-on-charcoal at 10% are added to a solution containing 1.5 g (3.5 mmol) of methyl (E)-3-(2-benzyloxy-4-methoxyphenyl)-2-(tert-butoxycarbonyl-amino)acrylate in 15 ml of methanol. After stirring for hours under a hydrogen atmosphere, the reaction medium is filtered through celite and the filtrate is evaporated off. 850 mg of methyl 2-tert-butoxycarbonylamino-3-(2-hydroxy-4-methoxyphenyl)-propanoate are obtained in the form of a grey powder with a yield of 74%.

Workup

  1. filtrationthe reaction medium is filtered through celite
  2. customthe filtrate is evaporated off

Sources & evidence

ORD record
ord-243080824efa4a04a21c0469e5a4c3f7
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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