Hydrochloric Acid → HCID 86709968, compound

HRID 1526797Notes

Reaction equation

HRID 1526797 reaction equation
[NH2:1][C@H:2]([C:7]1[CH:12]=[C:11]([C:13]2([CH:16]([F:18])[F:17])[CH2:15][CH2:14]2)[CH:10]=[C:9]([Br:19])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[ClH:20].[CH2:21](O)[CH3:22]>>[ClH:20].[NH2:1][C@H:2]([C:7]1[CH:12]=[C:11]([C:13]2([CH:16]([F:17])[F:18])[CH2:15][CH2:14]2)[CH:10]=[C:9]([Br:19])[CH:8]=1)[CH2:3][C:4]([O:6][CH2:21][CH3:22])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 86709970HCID 86709970, compound

Product 1

HCID 86709968HCID 86709968, compound

Procedure

To a solution of (S)-3-amino-3-(3-bromo-5-(1-(difluoromethyl)cyclopropyl)phenyl)propanoic acid (from step A above) (225.5 mg, 0.675 mmol) in absolute ethyl alcohol (3 mL) was added absolute ethanol saturated with anhydrous HCl gas (7 mL) and the reaction mixture was heated at reflux under nitrogen for 3 h to give a colorless solution. The solvent was evaporated in vacuo to give a colorless viscous liquid. The residue was triturated with diethyl ether (10 mL) and the solvent was evaporated in vacuo to give the desired (S)-ethyl 3-amino-3-(3-bromo-5-(1-(difluoromethyl)cyclopropyl)phenyl)propanoate hydrochloride salt as a colorless foamy solid (253.0 mg). LC-MS analysis of the solid shows the desired product's mass: m/z 362 (79BrM+H), m/z 364 (81BrM+H), m/z 384 (79BrM+Na) and m/z 386 (81BrM+Na); Calcd for C15H18BrF2NO2:362.21. The isolated solid will be used as such for the next step.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under nitrogen for 3 h
  3. customto give a colorless solution
  4. customThe solvent was evaporated in vacuo
  5. customto give a colorless viscous liquid
  6. customThe residue was triturated with diethyl ether (10 mL)
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bb8d49f90afc4677b39409b761c24adf
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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