(S)-mandelic acid → HCID 131719471, compound

HRID 1736339Notes

Reaction equation

HRID 1736339 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[O:21])[C:3]1=[O:29].[C:30]([OH:40])(=[O:39])[C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[OH:32]>C(#N)C.ClC1C=C(Cl)C=C(C=O)C=1O>[NH2:1][C@@H:2]1[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])=[O:21])[C:3]1=[O:29].[C:30]([O-:40])(=[O:39])[C@H:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[OH:32]

Participants

5

Reactant 2

HCID 439616(S)-mandelic acidHCID 10619983HCID 10619983, compound

Product 1

HCID 131719471HCID 131719471, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 666603,5-DichlorosalicylaldehydeCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 2.75 g 3-amino-1,3-dihydro-1-(2'-methylphenacyl)-5-phenyl-2H-1,4-benzodiazepin-2-one in 55 ml acetonitrile, was added 0.98 g (S)(+)-mandelic acid, the mixture was stirred at room temperature for 30 minutes, 41 mg 3,5-dichlorosalicylaldehyde was then added, and stirring was further continued for 18 hours. The crystals which separated out were collected by filtration and washed with 15 ml acetonitrile, thus giving 2.94 g of (R)-3-amino-1,3-dihydro-1-(2'-methylphenacyl)-5-phenyl-2H-1,4-benzodiazepin-2-one·(S)-mandelate.

Workup

  1. stirringstirring
  2. waitwas further continued for 18 hours
  3. customThe crystals which separated out
  4. filtrationwere collected by filtration
  5. washwashed with 15 ml acetonitrile

Sources & evidence

ORD record
ord-713c7dc68ab340dd905e0489b72cae87
Source dataset
uspto-grants-1996_07
Patent number
US05541182

Reaction notes

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