Hydrochloric Acid → HCID 67444615, compound

HRID 1255442Notes

Reaction equation

HRID 1255442 reaction equation
[F:1][C:2]1([F:18])[CH2:6][CH2:5][C@@H:4]([NH:7][C@H:8]([CH2:16][CH3:17])[C:9]([O:11][C:12](C)(C)C)=[O:10])[CH2:3]1.Cl>CO>[F:1][C:2]1([F:18])[CH2:6][CH2:5][C@@H:4]([NH:7][C@H:8]([CH2:16][CH3:17])[C:9]([O:11][CH3:12])=[O:10])[CH2:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67446056HCID 67446056, compound

Product 1

HCID 67444615HCID 67444615, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(R)-tert-butyl 2-((R)-3,3-difluorocyclopentyl amino)butanoate (1.0 g, 3.798 mmol) was dissolved in methanol (70 mL) and cooled down to 0° C. The resultant mixture was saturated with HCl gas, then stirred at room temperature for 3 hours. The reaction mixture was warmed to 40° C. for 90 minutes then concentrated under reduced pressure. The residue was partitioned between DCM and an aqueous solution of NaHCO3. The aqueous phase was extracted with DCM three times, dried over magnesium sulfate and concentrated under reduced pressure to afford the desired product as colourless oil (645 mg, 78% yield).

Workup

  1. temperatureThe reaction mixture was warmed to 40° C. for 90 minutes
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between DCM
  4. extractionThe aqueous phase was extracted with DCM three times
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e38e1e2d04e4588b545925acc31590c
Source dataset
uspto-grants-2013_06
Patent number
US08461149B2

Reaction notes

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