Sulfuric Acid → HCID 10052728, compound

HRID 969479Notes

Reaction equation

HRID 969479 reaction equation
S(=O)(=O)(O)O.COCCOC[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([CH2:25][NH:26][CH2:27][C:28]1[CH:29]=[C:30]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41]4[CH:42]=[C:43]([CH:49]=[CH:50][CH:51]=4)[C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:36][CH:35]=3)[CH:31]=[CH:32][CH:33]=1)=[O:24])[CH:17]=[CH:16]2>CO.O1CCCC1.C(OCC)(=O)C>[OH:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]=[C:18]([C:23]([CH2:25][NH:26][CH2:27][C:28]1[CH:29]=[C:30]([C:34]3[CH:39]=[CH:38][C:37]([NH:40][C:41]4[CH:42]=[C:43]([CH:49]=[CH:50][CH:51]=4)[C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:36][CH:35]=3)[CH:31]=[CH:32][CH:33]=1)=[O:24])[CH:17]=[CH:16]2

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 10008997HCID 10008997, compound

Product 1

HCID 10052728HCID 10052728, compoundYield 99.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 ml of concentrated sulfuric acid is added to a solution of 1.2 g (1.9 mmol) of ethyl 3-[3′-({[6-(2-methoxyethoxymethoxy)naphthalene-2-carbonyl]methylamino}methyl)biphenyl-4-ylamino]benzoate in 10 ml of methanol and 10 ml of tetrahydrofuran. The reaction medium is stirred at room temperature for 6 hours, diluted with ethyl acetate and washed with water. After extraction, the organic phase is dried over magnesium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 60/40 heptane/ethyl acetate mixture. 1 g of ethyl 3-(3′-{[(6-hydroxynaphthalene-2-carbonyl)methylamino]methyl}biphenyl-4-ylamino)benzoate is obtained in the form of a beige-colored foam, in a yield of 80%.

Workup

  1. washwashed with water
  2. extractionAfter extraction
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a 60/40 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-435f9cdf81db417bb703a4a38b62771a
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Reaction notes

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