Daidzein → Daidzein

HRID 1904879Notes

Reaction equation

HRID 1904879 reaction equation
[C:1]([NH:4][CH:5]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH:20]1[C:25]([C:26]2[C:31](=[O:32])[C:30]3[CH:33]=[CH:34][C:35]([OH:37])=[CH:36][C:29]=3[O:28][CH:27]=2)=[CH:24][CH:23]=[C:22]([OH:38])[CH:21]=1>C(O)C>[C:1]([NH:4][C@@H:5]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH:24]1[C:25]([C:26]2[C:31](=[O:32])[C:30]3[CH:33]=[CH:34][C:35]([OH:37])=[CH:36][C:29]=3[O:28][CH:27]=2)=[CH:20][CH:21]=[C:22]([OH:38])[CH:23]=1

Participants

5

Reactant 2

HCID 5281708DaidzeinHCID 13686282HCID 13686282, compound

Product 2

HCID 5281708DaidzeinHCID 13686283HCID 13686283, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 2-acetamido-4-(4-nitrophenyl)butyric acid (57.65 g) in hot 95% ethanol (1000 ml) add d-(+)-α-methylbenzylamine (25.2 g) in hot 95% ethanol (125 ml), cool the solution slowly and keep at room temperature 18 hours. Collect the solid and wash with cold 95% ethanol, and dry to give an orange-yellow solid. Recrystallize this solid from 95% ethanol treated with charcoal to give 2(S)-acetamido-4-(4-nitrophenyl)butyric acid, d-(+)-α-methylbenzyl amine salt [α]D26 =+45.6 (MeOH), m.p. 211°-213° C.

Workup

  1. temperaturecool the solution slowly
  2. customCollect the solid
  3. washwash with cold 95% ethanol
  4. customdry
  5. customto give an orange-yellow solid
  6. customRecrystallize this solid from 95% ethanol
  7. additiontreated with charcoal

Sources & evidence

ORD record
ord-8a7b12169c6c49678fe7110324dcfce9
Source dataset
uspto-grants-1989_06
Patent number
US04840772

Reaction notes

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