1-Phenethylamine, (+)- → HCID 57529283, compound

HRID 1454205Notes

Reaction equation

HRID 1454205 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:39]1([C@H:45]([NH2:47])[CH3:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([C:5](=[O:7])[NH:47][C@@H:45]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH3:46])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 3

HCID 6431891-Phenethylamine, (+)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 57529283HCID 57529283, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-5-(methoxycarbonyl)benzoic acid (0.60 g, 2.32 mmol) and HATU (1.06 g, 2.78 mmol) in DMF (15 mL) was stirred at room temperature for 10 min. Then (R)-1-phenylethanamine (0.28 g, 0.3 mL, 2.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with H2O (3 times) and brine, dried over sodium sulfate, and concentrated under vacuum to give the title compound (0.839 g, 99.9% yield): HPLC retention time: 2.17 min (method A). MS (ESI) (M+H)+ 362/364.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washwashed with H2O (3 times) and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d337da6b2d354399a258b5a34154a708
Source dataset
uspto-grants-2009_01
Patent number
US07476764B2

Reaction notes

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