(E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate → Ethyl 3-(3-((tert-butoxycarbonyl)amino)-4-chlorophenyl)propanoate

HRID 2167662Notes

Reaction equation

HRID 2167662 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:12]=[CH:13][C:14]=1[Cl:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67067541(E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 67065553Ethyl 3-(3-((tert-butoxycarbonyl)amino)-4-chlorophenyl)propanoate

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of (E)-ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)acrylate (6-3) (1.0 equiv.) in ethyl acetate/ethanol (1:1, 0.3 M) was added Wilkinson's catalyst (0.10 equiv.). Hydrogen gas was introduced via a ballon, and the reaction was stirred at room temperature for 24 hours. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated in vacuo and purified by Combiflash using 0-10% ethyl acetate in hexane to give ethyl 3-(3-(tert-butoxycarbonylamino)-4-chlorophenyl)propanoate (6-4) as a solid.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified by Combiflash

Sources & evidence

ORD record
ord-872f22a2b6d34d1c8ba6b71c8d536158
Source dataset
uspto-grants-2015_06
Patent number
US09045470B2

Reaction notes

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