1-Phenethylamine, (+)- → (-)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid (R)-(+)-alpha-methylbenzylamine salt

HRID 1979489Notes

Reaction equation

HRID 1979489 reaction equation
[CH3:1][C@@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([C:14]([CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH:19]([NH:34][C:35](=[O:46])[NH:36][C:37]2[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=2)[C:40]([OH:42])=[O:41])[C:18]1=[O:47])=[O:15])([CH3:13])([CH3:12])[CH3:11]>CC(O)C>[CH3:1][C@@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:10]([C:14]([CH2:16][N:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:20][CH:19]([NH:34][C:35](=[O:46])[NH:36][C:37]2[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=2)[C:40]([OH:42])=[O:41])[C:18]1=[O:47])=[O:15])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 6431891-Phenethylamine, (+)-HCID 227094293-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid

Product 1

HCID 86756981(-)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid (R)-(+)-alpha-methylbenzylamine saltYield 17.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(R)-(+)-α-methylbenzylamine (242 mg) was added to a solution of (±)-3-[3-(1-tert-butylcarbonylmethyl-2-oxo-5-phenyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl)ureido]benzoic acid (1.03 g) in 2-propanol (20 ml), the mixture was stirred overnight. Crystals so precipitated were collected by filtration, the crystals were recrystallized from 2-propanol, to thereby obtain 220 mg of the title compound.

Workup

  1. customCrystals so precipitated
  2. filtrationwere collected by filtration
  3. customthe crystals were recrystallized from 2-propanol

Sources & evidence

ORD record
ord-e5e7e88325f14d449d7c2f0491d53ccf
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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