Hydrochloric Acid → HCID 86709963, compound

HRID 1526794Notes

Reaction equation

HRID 1526794 reaction equation
Cl.[NH2:2][C@H:3]([C:8]1[CH:13]=[C:12]([C:14]([CH3:20])([CH3:19])[C:15]([F:18])([F:17])[F:16])[CH:11]=[C:10]([Cl:21])[CH:9]=1)[CH2:4][C:5]([OH:7])=[O:6].[CH2:22](OCC)[CH3:23]>C(O)C>[ClH:21].[NH2:2][C@H:3]([C:8]1[CH:13]=[C:12]([C:14]([CH3:19])([CH3:20])[C:15]([F:16])([F:17])[F:18])[CH:11]=[C:10]([Cl:21])[CH:9]=1)[CH2:4][C:5]([O:7][CH2:22][CH3:23])=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86709965HCID 86709965, compound

Product 1

HCID 86709963HCID 86709963, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Absolute ethanol saturated with anhydrous HCl gas (10 mL) was added to a suspension of (S)-3-amino-3-(3-chloro-5-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl)propanoic acid (from step A above) (252.8 mg, 0.816 mmol) in absolute ethyl alcohol (5 mL) and the reaction mixture was heated at reflux for 4 h to give a colorless solution. The solvent was removed in vacuo to give a colorless gummy solid. The solid was slurried a couple of times with diethyl ether (2×5 mL). After the solvent was decanted off, the residue was dried in vacuo to give the desired (S)-ethyl 3-amino-3-(3-chloro-5-(1,1,1-trifluoro-2-methylpropan-2-yl)phenyl)propanoate hydrochloride salt as a cream foamy solid (293.76 mg). LC-MS analysis of the solid shows the desired product's mass: m/z 338 (35ClM+H), m/z 340 (37ClM+H), m/z 360 (35ClM+Na) and m/z 362 (37ClM+Na); Calcd for C15H19ClF3NO2: 337.77.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. customto give a colorless solution
  4. customThe solvent was removed in vacuo
  5. customto give a colorless gummy solid
  6. customAfter the solvent was decanted off
  7. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-7e9a0e58c4da4180a71284fc0768d235
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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