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Hydrochloric Acid → N-benzoylphenylalanyltyrosine

HRID 2398852
Notes
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Reaction equation

HRID 2398852 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 1 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 C25H24O5N2 : C, 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-f8ac1bca6b57479a87c9e007a005e7e8
Source dataset
uspto-grants-1977_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04025644

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes