Hydrogen Peroxide → HCID 54435591, compound

HRID 1017987Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][C@@H:10]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=3)=[CH:17][CH:16]=2)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])[CH:2]=1.[OH:44]O>C(O)(=O)C>[O-:44][N+:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([NH:9][C@@H:10]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:43])[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=4[CH3:40])=[O:32])=[C:26]([O:41][CH3:42])[CH:25]=3)=[CH:17][CH:16]=2)[CH2:11][C:12]([OH:14])=[O:13])=[O:8])[CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (R)-3-[(pyridine-3-carbonyl)amino]-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]-phenylacetylamino}phenyl)-propanoic acid [0.4 g, Example 5(e)], acetic acid (2.5 ml) and hydrogen peroxide (0.5 ml) was stirred at 80° C. for 6 hours. The reaction mixture was evaporated and the residue was triturated with water. The resulting solid was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane, methanol and acetic acid (9:1:0.5, v/v/v) to give the title compound as a light brown solid (50 mg), m.p. 190° C. (with decomposition). MS: MH+ 598.

Workup

customThe reaction mixture was evaporated
customthe residue was triturated with water
additionThe resulting solid was subjected to flash chromatography on silica gel eluting with a mixture of dichloromethane, methanol and acetic acid (9:1:0.5

Sources & evidence

ORD record: ord-7a4614c7639c4881aa7f7c4b37b1b3f1
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479519B1

Reaction notes

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