2-Tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-acrylic acid methyl ester → (R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2,5-difluorophenyl)propanoate

HRID 424979Notes

Reaction equation

HRID 424979 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[F:13]>CO.[B-](F)(F)(F)F.CC[C@H]1P(C2C(P3[C@H](CC)CC[C@H]3CC)=CC=CC=2)[C@H](CC)CC1.C1[CH][CH]CC[CH][CH]C1.[Rh]>[CH3:1][O:2][C:3](=[O:22])[C@H:4]([NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[F:13]

Participants

4

Reactant 1

HCID 667036742-Tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-acrylic acid methyl ester

Product 1

HCID 11255500(R)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2,5-difluorophenyl)propanoateYield 98.1%

Reagents, catalysts & solvents 2

HCID 11549211CID 11549211CatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-acrylic acid methyl ester (4.9 g, 15.7 mmol) in methanol (49 mL) is added (−)-1,2-bis((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) tetrafluoroborate (113 mg, 0.15 mmol), and is shaken for 20 h under an atmosphere of H2 at 75 psi. The suspension is filtered through Celite to remove catalyst and concentrated under reduced pressure to afford a light yellow solid. The solid is triturated in cold methanol to afford the title compound as a white solid (4.75 g, 15.4 mmol)

Workup

  1. filtrationThe suspension is filtered through Celite
  2. customto remove catalyst
  3. concentrationconcentrated under reduced pressure
  4. customto afford a light yellow solid
  5. customThe solid is triturated in cold methanol

Sources & evidence

ORD record
ord-1ec6a794a504458a893e05361438178e
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Reaction notes

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