Water → HCID 10028788, compound

HRID 1072108Notes

Reaction equation

HRID 1072108 reaction equation
COCCOC[O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]([N:20]([CH2:22][C:23]1[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH:36]4[S:40][C:39](=[O:41])[NH:38][C:37]4=[O:42])=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=1)[CH3:21])=[O:19])[CH:12]=[CH:11]2.S(=O)(=O)(O)O.O>O1CCCC1.CO>[OH:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[CH:14]=[C:13]([C:18]([N:20]([CH2:22][C:23]1[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][CH:36]4[S:40][C:39](=[O:41])[NH:38][C:37]4=[O:42])=[CH:31][CH:30]=3)[CH:26]=[CH:27][CH:28]=1)[CH3:21])=[O:19])[CH:12]=[CH:11]2

Participants

6

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 10393495HCID 10393495, compound

Product 1

HCID 10028788HCID 10028788, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g (2.5 mmol) of 6-(2-methoxyethoxymethoxy)-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylnaphthalene-2-carboxamide (obtained in Example 16) in 10 ml of tetrahydrofuran and 10 ml of methanol are introduced into a round-bottomed flask. 500 μl of concentrated sulphuric acid are added and the medium is stirred for 2 hours at room temperature. Water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and then evaporated off. The residue is purified by chromatography on a silica column eluted with a heptane and ethyl acetate (30/70) mixture. 1.26 g (99%) of 6-hydroxy-N-[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]-N-methylnaphthalene-2-carboxamide are obtained in the form of a white powder having a melting point of 218° C.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated off
  5. customThe residue is purified by chromatography on a silica column
  6. washeluted with a heptane and ethyl acetate (30/70) mixture

Sources & evidence

ORD record
ord-d135514ce0314a2494fcb632a6b556ae
Source dataset
uspto-grants-2005_06
Patent number
US06908939B2

Reaction notes

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