1-Phenethylamine, (-)- → HCID 14478556, compound

HRID 1199320Notes

Reaction equation

HRID 1199320 reaction equation
[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C:20]([O:24][C:25]([C:27]1[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:26])([C:22]#[CH:23])[CH3:21])(=[O:3])[CH3:2].[CH3:36][C@H:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(O)C.C(OCC)C>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C@:20]([O:24][C:25]([C:27]1[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:26])([C:22]#[CH:23])[CH3:21])(=[O:3])[CH3:2].[CH3:36][C@@H:37]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH2:44]

Participants

5

Reactant 2

HCID 758181-Phenethylamine, (-)-HCID 14478552HCID 14478552, compound

Product 1

HCID 14478556HCID 14478556, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 27.00 g (0.056 mol) of rac-1,2-benzenedicarboxylic acid [3-[2,5-bis(acetyloxy)-3,4,6-trimethylphenyl]-1-ethynyl-1-methylpropyl]ester in 50 mL of 95% ethanol was added, with stirring 7.02 (0.058 mol) of (S)-(-)-α-methylbenzylamine in 250 mL of diethylether. The resulting solution was stirred at 25° C. for 0.5 h, then cooled in an ice bath until crystallization occured. It was further stirred at 0° C. for 0.5 h and the crystals were collected and air dried to give 16 g of white solid. This white solid was dissolved in 50 mL of ethanol (95%) and 150 mL of diethylether. The solution was kept at 25° C. for approximately 1.0 h and crystallization occurred. It was further stored at 0° C. for 1.0 h and the crystals were collected, dried at 25° C./0.5 mm for 24 h to yield 10.1 g of (S)-1,2-benzenedicarboxylic acid[3-[2,5-bis(acetyloxy)3,4,6-trimethylphenyl]-1-ethynyl-1-methylpropyl]ester(S)-α-methyl benzenemethanamine (1:1) (salt) as a white solid (30% yield from racemic starting materials), m.p. 162°-165° C.

Workup

  1. temperaturecooled in an ice bath until crystallization
  2. stirringIt was further stirred at 0° C. for 0.5 h
  3. customthe crystals were collected
  4. customair dried

Sources & evidence

ORD record
ord-4722f5d7dbb04bfeb886af89fa02b125
Source dataset
uspto-grants-1990_02
Patent number
US04900476

Reaction notes

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