4-Nitrophenol → HCID 66703782, compound

HRID 424980Notes

Reaction equation

HRID 424980 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23]>ClCCl>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:11][C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 11335616Boc-2,5-difluoro-D-phenylalanine

Product 1

HCID 66703782HCID 66703782, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-tert-butoxycarbonylamino-3-(2,5-difluorophenyl)-propionic acid (8.0 g, 27 mmol) in anhydrous dichloromethane (200 mL) at 0° C. is added N-ethyl-N′,N′-dimethylaminoethyl carbodiimide (5.09 g, 27 mmol), followed by 4-nitrophenol (4.4 g, 32 mmol). After stirring for 30 min, the solution is washed sequentially with saturated NaHCO3 (aq), water, 1.0 M citric acid (aq), water and brine, then dried over Na2SO4 and concentrated under reduced pressure to afford the title compound as a slightly red solid (8.11 g, 19 mmol), contaminated with residual 4-nitrophenol, which may be used without purification.

Workup

  1. washthe solution is washed sequentially with saturated NaHCO3 (aq), water, 1.0 M citric acid (aq), water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e205bd388e34da4bdb8740eca7b3970
Source dataset
uspto-grants-2012_01
Patent number
US08106090B2

Reaction notes

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