Water → HCID 19996384, compound

HRID 2248505Notes

Reaction equation

HRID 2248505 reaction equation
C([O:8][C:9](=[O:35])[CH2:10][CH2:11][NH:12][C:13](=[O:34])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21](=[O:33])[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]=[N+]=[N-])=[CH:25][CH:24]=2)[CH:15]=1)C1C=CC=CC=1.O>C(O)(=O)C.[Pd]>[NH2:30][CH2:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][C:21]([NH:20][C:16]2[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=2)[C:13]([NH:12][CH2:11][CH2:10][C:9]([OH:35])=[O:8])=[O:34])=[O:33])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19996373HCID 19996373, compound

Product 1

HCID 19996384HCID 19996384, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

296 mg of N-[m-[2-(α-azido-p-tolyl)acetamido]benzoyl]-β-alanine benzyl ester and 74 mg of Pd/C are stirred in 6 ml of acetic acid for 7 hours under hydrogen. After the addition of 3 ml of water the mixture is filtered and the filtrate is evaporated in a vacuum. The residue is taken up in water and the suspension is evaporated in a vacuum. The residue is triturated in methanol, filtered off under suction and dried. There are obtained 125 mg of N-[m-[2-(α-amino-p-tolyl)acetamido]benzoyl]-β-alanine (3:4 hydrate), m.p. 226° C.

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated in a vacuum
  3. customthe suspension is evaporated in a vacuum
  4. customThe residue is triturated in methanol
  5. filtrationfiltered off under suction
  6. customdried

Sources & evidence

ORD record
ord-77e25586d91a41dc8ca71509335f997e
Source dataset
uspto-grants-1991_08
Patent number
US05039805

Reaction notes

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