1-Phenethylamine, (+)- → HCID 86638377, compound

HRID 1096192

Reaction equation

HRID 1096192 reaction equation
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([NH:21][CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18]>C(OC(C)C)(C)C.CO>[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:10][C:11]1[CH:12]=[C:13]([NH:21][CH:22]([CH3:26])[C:23]([OH:25])=[O:24])[CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 66782716HCID 66782716, compound

Product 1

HCID 86638377HCID 86638377, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 21882575Diisopropylether methanolSolvent2×

Procedure

A solution of (R)-(+)-1-phenylethylamine (104 mg, 0.86 mmol) in diisopropyl ether/MeOH 20:1 (4.5 mL) was added dropwise at RT to a solution of 2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (417 mg, 1.56 mmol) in diisopropyl ether/MeOH 20:1 (4.5 mL), then after 2 h the precipitate was collected by filtration, washed with diisopropyl ether, and dried under vacuum. This material was digested in chloroform (3 mL) at 50° C. for 18 h, then collected by filtration, and dried under vacuum to afford 2-(3-chloro-4-trifluoromethyl-phenylamino)-propionic acid (R)-(+)-1-phenylethylamine salt (187 mg). This salt was partitioned between 10% aq. KHSO4 solution and EtOAc. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (134 mg, 32%) in an enantiomeric ratio of 98.5:1.5. White solid.

Workup

  1. filtrationafter 2 h the precipitate was collected by filtration
  2. washwashed with diisopropyl ether
  3. customdried under vacuum
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-35e02b62ad7441899f74e26ace30d64e
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Linked notes

Loading…