Trifluoroacetic acid → (R)-6-Amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester

HRID 885509Notes

Reaction equation

HRID 885509 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([F:25])=[C:20]([CH3:26])[CH:19]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH:9]C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:17][C:18]1[CH:23]=[C:22]([CH3:24])[C:21]([F:25])=[C:20]([CH3:26])[CH:19]=1)[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69188199HCID 69188199, compound

Product 1

HCID 69169741(R)-6-Amino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl esterYield 81.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-tert-butoxycarbonylamino-2-(4-fluoro-3,5-dimethyl-phenylamino)-hexanoic acid methyl ester (2.000 g, 5.232 mmol) in 10 mL of dichloromethane, was added trifluoroacetic acid (10 mL). After stirring at room temperature for 19 h, the reaction mixture was concentrated under reduced pressure, and dried in vacuum for overnight. The crude product (1.200 g, 81% yield) was used directly in the next step without further purification. LC-MS: tR=4.8 min; m/z 283 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customdried in vacuum for overnight

Sources & evidence

ORD record
ord-4924f287920f469bbc15cb77516ad97f
Source dataset
uspto-grants-2012_08
Patent number
US08242174B2

Reaction notes

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