Nitric Acid → HCID 67452110, compound

HRID 1852367Notes

Reaction equation

HRID 1852367 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH2:4][N:5]([C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[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]([CH3:17])=[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

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 67451206HCID 67451206, compound

Product 1

HCID 67452110HCID 67452110, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
30 °C

Procedure

50 g ((2-(2-(2-(Bis-methoxycarbonylmethyl-amino)-phenoxy)-ethoxy)-4-methyl-phenyl)-methoxycabonylmethyl-amino)-acetic acid methyl ester were dissolved in 600 ml glacial acetic acid. Under vigorous stirring 91.5 ml 1 molar nitric acid in glacial acetic acid was added and in a second step 28 ml of concentrated sulfuric acid was added. The temperature increased up to 30° C. The reaction mixture was directly poured in a 10 l 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. The product was finally crystallized from propan-2-ol. Yield: 20 g.

Workup

  1. additionwas added
  2. filtrationThe residue was filtered off
  3. washwashed several times with water
  4. customdried under vacuum
  5. customThe crude product was further purified by column chromatography on silica gel first with hexane/acetic acid ethyl ester (1:1) as eluent
  6. customThe product was finally crystallized from propan-2-ol

Sources & evidence

ORD record
ord-3905aa4bd5eb45f7ad626a8c6fd2c976
Source dataset
uspto-grants-2015_02
Patent number
US08962338B2

Reaction notes

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