HCID 86646666, compound → HCID 86646668, compound

HRID 1799213Notes

Reaction equation

HRID 1799213 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[N+:22]([O-])=O>C(O)(=O)C.O.[Fe]>[NH2:22][C:3]1[CH:4]=[C:5]([C@H:8]([CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:18])[F:19])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 1

HCID 86646666HCID 86646666, compound

Product 1

HCID 86646668HCID 86646668, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl (3R)-3-(4-chloro-3-nitrophenyl)-4-(2,2,2-trifluoroacetylamino)butanoate (65a) (3 g, 8.15 mmol) was dissolved in 4 mL of acetic acid and 60 mL of water. At 50° C., iron powder (2.5° C., 2.74 g, 40.75 mmol) was added and the reaction mixture was stirred for 1 h at 50° C. The mixture was cooled to room temperature and then extracted with 100 mL of ethyl acetate. The ethyl acetate solution was washed with 30 mL of water, and the water extraction repeated another ten times to remove the acetic acid. The organic layer was dried over sodium sulfate and the solvent removed under reduced pressure to provide 2.1 g of methyl (3R)-3-(3-amino-4-chlorophenyl)-4-(2,2,2-trifluoroacetylamino)butanoate (65b).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with 100 mL of ethyl acetate
  3. washThe ethyl acetate solution was washed with 30 mL of water
  4. extractionthe water extraction
  5. customto remove the acetic acid
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-6ed7a56e14d346ef88e2cf7ec9eadba5
Source dataset
uspto-grants-2013_01
Patent number
US08344028B2

Reaction notes

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