(S)-mandelic acid → HCID 131719470, compound

HRID 1736338Notes

Reaction equation

HRID 1736338 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](=[O:27])[C:21]2[S:25][CH:24]=[CH:23][C:22]=2[CH3:26])[C:3]1=[O:28].[C:29]([OH:39])(=[O:38])[C@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:31]>ClC1C=C(Cl)C=C(C=O)C=1O.C(#N)C>[NH2:1][C@@H: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](=[O:27])[C:21]2[S:25][CH:24]=[CH:23][C:22]=2[CH3:26])[C:3]1=[O:28].[C:29]([O-:39])(=[O:38])[C@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:31]

Participants

5

Reactant 2

HCID 439616(S)-mandelic acidHCID 10715372HCID 10715372, compound

Product 1

HCID 131719470HCID 131719470, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 666603,5-DichlorosalicylaldehydeCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4.28 g 3-amino-1,3-dihydro-1-(3-methyl-2-thenoyl)methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 1.59 g (S)-mandelic acid, 63 mg 3,5-dichlorosalicylaldehyde and 110 ml acetonitrile was stirred at room temperature for three days. The crystals which separated out were collected by filtration and washed with 100 ml acetonitrile, thus giving 5.13 g of (R)-3-amino-1,3-dihydro-1-(3-methyl-2-thenoyl)methyl-5-phenyl-2H-1,4-benzodiazepin-2-one·(S)mandelate as white crystals.

Workup

  1. customThe crystals which separated out
  2. filtrationwere collected by filtration
  3. washwashed with 100 ml acetonitrile

Sources & evidence

ORD record
ord-b4e2c95a4e7740de96b823376515f15e
Source dataset
uspto-grants-1996_07
Patent number
US05541182

Reaction notes

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