DL-alanine → HCID 54260365, compound

HRID 839954Notes

Reaction equation

HRID 839954 reaction equation
[NH2:1][CH:2]([C:4]([OH:6])=[O:5])[CH3:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:19]1([C:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[N+]=[N-])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.O.CN(C)C=O>[NH2:1][CH:2]([C:4]([O:6][CH:25]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:5])[CH3:3]

Participants

8

Reactant 4

HCID 602DL-alanineHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 54260365HCID 54260365, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

9.0 g. of D,L-alanine and 19.0 g. of p-toluenesulfonic acid monohydrate are dissolved in 50 ml. of dimethylformamide. 21.1 g. of diphenyldiazomethane in 100 ml. of dimethylformamide are added dropwise at 50°. This mixture is stirred for 1 hour at 50° and then the solvent is distilled off in vacuum. The oily residue solidifies upon treatment with ether. The D,L-alanine, diphenylmethyl ester p-toluenesulfonate salt is recrystallized from acetonitrile and is obtained as white crystals, yield 13.5 g.; m.p. 170°-172°. 30 g. of this salt are dissolved in 200 ml. of water, layered over with 200 ml. of chloroform and 10 g. of sodium bicarbonate are added with frequent agitation. The organic phase is washed with 50 ml. of water, dried over sodium sulfate and evaporated. 17 g. of white crystalline D,L-alanine, diphenylmethyl ester are obtained, m.p. 60°-62°.

Workup

  1. distillationthe solvent is distilled off in vacuum
  2. customThe D,L-alanine, diphenylmethyl ester p-toluenesulfonate salt is recrystallized from acetonitrile
  3. customis obtained as white crystals, yield 13.5 g
  4. dissolutionof this salt are dissolved in 200 ml
  5. washThe organic phase is washed with 50 ml
  6. dry with materialof water, dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-d649087e56b84e61ab22b9d1c358d810
Source dataset
uspto-grants-1978_06
Patent number
US04097670

Reaction notes

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