Nitric Acid → HCID 67451921, compound

HRID 1852370Notes

Reaction equation

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

Participants

Conditions

Temperature: 30 °C

Procedure

2.5 g ((2-(2-(2-(Bis-methoxycarbonylmethyl-amino)-phenoxy)-ethoxy)-4-fluoro-phenyl)-methoxycabonylmethyl-amino)-acetic acid methyl ester were dissolved in 30 ml glacial acetic acid. Under vigorous stirring 4.54 ml 1 molar nitric acid in glacial acetic acid was added and in a second step 11.35 ml of concentrated sulfuric acid was added. The temperature increased up to 30° C. The reaction mixture was directly poured in a 250 ml ice/water mixture. The residue was filtered off, washed several times with water and dried under vacuum. The crude product was further purified by column chromatography on silica gel first with hexane/acetic acid ethyl ester (1:1) as eluent and a second time with toluene/acetonitrile (1:1) as eluent. Yield: 0.82 g.

Workup

additionwas added
filtrationThe residue was filtered off
washwashed several times with water
customdried under vacuum
customThe crude product was further purified by column chromatography on silica gel first with hexane/acetic acid ethyl ester (1:1) as eluent

Sources & evidence

ORD record: ord-d56bb863645a4a45973330f6dbe2cb7f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962338B2

Reaction notes

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