Hydrochloric Acid → N-benzoylphenylalanyltyrosine

HRID 1439003Notes

Reaction equation

HRID 1439003 reaction equation
[C:1]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:30]([O:32]C)=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[C:1]([NH:9][C@H:10]([C:18]([NH:20][C@H:21]([C:30]([OH:32])=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 44241224methyl N-benzoylphenylalanyltyrosinate

Product 1

HCID 44241045N-benzoylphenylalanyltyrosineYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol, 4.4 g of methyl N-benzoylphenylalanyltyrosinate was dissolved. After addition of 23 ml of 1 N sodium hydroxide, the solution was stirred for one hour. The reaction mixture was neutralized with hydrochloric acid, concentrated and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to dryness. The residue was crystallized from ethyl acetate to give 3.8 g of N-benzoylphenylalanyltyrosine with a mp. 191°-192° C, in a yield of 87%. Analysis, calculated for C25H24O5N2C 69.43, H 5.59, N 6.48, found C 68.98, H 5.72, N 6.37.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9c5901a0060446a0b12014508f6cdd2a
Source dataset
uspto-grants-1977_11
Patent number
US04057629

Reaction notes

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