Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate → Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate

HRID 449504Notes

Reaction equation

HRID 449504 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 67542936Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate

Product 1

HCID 23033930Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoateYield 100.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate (0.92 g, 3.1 mmol) was dissolved in methanol (30 ml) in a Parr shaker bottle. This was degassed with nitrogen and the 10% Pd/C catalyst was added. The reaction was charged with hyrodgen to 55 Psi, and shaken for 3 h. The reaction was complete, the catalyst filtered off and the methanol removed under reduced pressure to give methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)propanoate (0.92 g, 100%) as a oil. Analytical LCMS (M+H-Boc)+: m/z=195.9.

Workup

  1. customThis was degassed with nitrogen
  2. additionthe 10% Pd/C catalyst was added
  3. additionThe reaction was charged with hyrodgen to 55 Psi
  4. filtrationthe catalyst filtered off
  5. customthe methanol removed under reduced pressure

Sources & evidence

ORD record
ord-522dd92afc13405a8592a248bb8632de
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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