Hydrogen Peroxide → HCID 131713561, compound

HRID 1262885Notes

Reaction equation

HRID 1262885 reaction equation
[OH2:1].[ClH:2].[CH3:3][NH:4][C@H:5]([C:14]([NH:16][C@@H:17]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:23])[CH2:18][CH2:19][S:20][CH3:21])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.OO>C(O)(=O)C>[OH2:13].[ClH:2].[CH3:3][NH:4][C@H:5]([C:14]([NH:16][C@@H:17]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:23])[CH2:18][CH2:19][S:20](=[O:1])[CH3:21])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1.[CH3:3][NH:4][C@H:5]([C:14]([NH:16][C@@H:17]([C:22]([NH:24][CH2:25][CH2:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:23])[CH2:18][CH2:19][S:20](=[O:1])[CH3:21])=[O:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1.[ClH:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 70510552HCID 70510552, compound

Product 1

HCID 131713561HCID 131713561, compoundYield 119.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-methyl-L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride hydrate (4:1) (690 mg.) and aqueous hydrogen peroxide (3%, 1.95 ml.) in acetic acid (10 ml.) was stirred at room temperature, then stripped of volatiles. The residue was purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.) using ammonium acetate (0.2%) in methanol-water (1:1) as the eluant. A solution of the product, which appeared in fractions 4-5 (centered at k'=2.0), in methanol (20 ml.) and hydrochloric acid (0.01 N, 100 ml.) was concentrated (to 60 ml.), filtered and lyophilized, affording as an amorphous solid N-methyl-L-tyrosyl-N-(3-phenylpropyl)-D-methioninamide S-oxide monohydrochloride hemihydrate (558 mg.; [α]D25 +59.8°, c=1, methanol), whose free base is the compound of Formula II wherein Q is Met(O), R1 is methyl, R2 and R5 are each hydrogen and R4 is (CH2)nY wherein n is 3 and Y is phenyl.

Workup

  1. customThe residue was purified by reverse phase high pressure liquid chromatography on octadecylsilated silica gel (350 g.)
  2. concentrationhydrochloric acid (0.01 N, 100 ml.) was concentrated (to 60 ml.)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-0c6004c66c1745ebb866daf2d3c8d51a
Source dataset
uspto-grants-1984_06
Patent number
US04454120

Reaction notes

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