Hydrogen Peroxide → HCID 86739482, compound

HRID 1262882Notes

Reaction equation

HRID 1262882 reaction equation
[ClH:1].[NH2:2][C@H:3]([C:12]([NH:14][C@@H:15]([C:20]([N:22]([CH3:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:21])[CH2:16][CH2:17][S:18][CH3:19])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[OH:33]O>C(O)(=O)C>[OH2:11].[ClH:1].[NH2:2][C@H:3]([C:12]([NH:14][C@@H:15]([C:20]([N:22]([CH3:32])[CH2:23][CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:21])[CH2:16][CH2:17][S:18](=[O:33])[CH3:19])=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 70511483HCID 70511483, compound

Product 1

HCID 86739482HCID 86739482, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride (1.3 g.) and aqueous hydrogen peroxide (3%, 2.7 ml.) in acetic acid (10 ml.) was stirred at room temperature for two hours, the concentrated. The residue was evaporated twice from ethyl acetate then purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.) using ammonium acetate (0.15%) in methanol-water (3:2) as the eluant (200 ml./min.). A solution of the product (1.0 g.), which appeared in fraction 2 (k'=1.4-3.0), in hydrochloric acid (0.0936N, 30 ml.) and water (30 ml.) was lyophilized, affording L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide S-oxide monohydrochloride monohydrate ([α]D25 +61.4°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met(O), R1 and R2 are each hydrogen, R4 is (CH2)nY wherein n is 3 and Y is phenyl and R5 is methyl.

Workup

  1. customThe residue was evaporated twice from ethyl acetate
  2. customthen purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.)

Sources & evidence

ORD record
ord-9c08c76cf5f04b8b9a8f7eee254be649
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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