1-Phenethylamine, (-)- → HCID 86758414, compound

HRID 2303975Notes

Reaction equation

HRID 2303975 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:24]1([C@@H:30]([NH2:32])[CH3:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1CCN2C(=NCCC2)CC1>CC(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:24]1([C@@H:30]([NH2:32])[CH3:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 758181-Phenethylamine, (-)-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 17818832HCID 17818832, compound

Product 1

HCID 86758414HCID 86758414, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

176.60 g (0.500 mol) of 3-(3,4-dichlorophenyl)-3-benzyloxycarbonylpropionic acid was suspended in 1,250 ml of 2-propanol and the solution was heated to an internal temperature of 70° C. Then 60.59 g (0.500 mol) of (S)-1-phenylethylamine and 6.09 g (0.040 mol) of DBU were added and the solution was heated to an internal temperature of 75° C. and stirred. With this temperature maintained, the solution was further stirred for 3 hours, then cooled slowly to an internal temperature of 30° C. and additionally stirred at this temperature for 2 hours. The precipitated crystals were filtered by a Nutsche funnel and then washed thrice with 250 ml of 2-propanol to obtain 177.40 g (72.9% yield) of (+)-3-(3,4-dichlorophenyl)-3-benzyloxycarbonylpropionic acid·(S)-1-phenylethylamine salt.

Workup

  1. temperaturethe solution was heated to an internal temperature of 75° C.
  2. temperatureWith this temperature maintained
  3. stirringthe solution was further stirred for 3 hours
  4. temperaturecooled slowly to an internal temperature of 30° C.
  5. stirringadditionally stirred at this temperature for 2 hours
  6. filtrationThe precipitated crystals were filtered by a Nutsche funnel
  7. washwashed thrice with 250 ml of 2-propanol

Sources & evidence

ORD record
ord-28bb1bde06f84f43a639dbdb5a5d1e36
Source dataset
uspto-grants-2002_08
Patent number
US06433174B1

Reaction notes

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