Hydrogen Peroxide → HCID 131713559, compound

HRID 1262878Notes

Reaction equation

HRID 1262878 reaction equation
[OH2:1].[ClH:2].[NH2:3][C@H:4]([C:13]([NH:15][C@@H:16]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22])[CH2:17][CH2:18][S:19][CH3:20])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.OO>C(O)(=O)C>[OH2:12].[ClH:2].[NH2:3][C@H:4]([C:13]([NH:15][C@@H:16]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:22])[CH2:17][CH2:18][S:19](=[O:1])[CH3:20])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[OH2:12].[OH2:12].[NH2:3][C@H:4]([C:13]([NH:15][C@@H:16]([C:21]([NH:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:22])[CH2:17][CH2:18][S:19](=[O:1])[CH3:20])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[ClH:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 70511677HCID 70511677, compound

Product 1

HCID 131713559HCID 131713559, compoundYield 244.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride monohydrate (219 mg.) and aqueous hydrogen peroxide (3%, 640 μl) in acetic acid (5 ml.) was stirred at room temperature for two and one quarter hours, then concentrated under vacuum. The residue was reevaporated under vacuum once from ethyl acetate and three times from ether. A solution of the residue in water was filtered and lyophilized, affording as an amorphous white solid L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide S-oxide monohydrochloride sesquihydrate (225 mg.), whose free base is the compound of Formula II wherein Q is Met(O), R1, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was reevaporated under vacuum once from ethyl acetate and three times from ether
  3. filtrationA solution of the residue in water was filtered

Sources & evidence

ORD record
ord-73e2acdaf5a54897bbb57723793b83d2
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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