Hydrochloric Acid → HCID 10114552, compound

HRID 584974Notes

Reaction equation

HRID 584974 reaction equation
C(=O)([O-])O.[Na+].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:40])[N:17]([CH2:19][C:20]2[CH:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH:33]4[S:37][C:36](=[O:38])[NH:35][C:34]4=[O:39])=[CH:28][CH:27]=3)[CH:23]=[CH:24][CH:25]=2)[CH3:18])=[CH:12][CH:11]=1)(=O)C.Cl>O1CCCC1.O.C(OC(=O)C)C>[O:38]=[C:36]1[NH:35][C:34](=[O:39])[CH:33]([CH2:32][C:29]2[CH:28]=[CH:27][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][N:17]([CH3:18])[C:16](=[O:40])[C:13]4[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=4)[CH:21]=3)=[CH:31][CH:30]=2)[S:37]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10228108HCID 10228108, compound

Product 1

HCID 10114552HCID 10114552, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

110 mg (1.3 mmol) of sodium hydrogen carbonate are added to 350 mg (6.7 mmol) of 4-{[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}phenyl acetate (obtained in Example 56) in 5 ml of tetrahydrofuran and 500 μl of water. The reaction medium is stirred at room temperature for 48 hours and then diluted in ethylacetate and acidified to pH 3-4 with 1N hydrochloric acid solution. The organic phase is separated out after settling of the phases has taken place, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a 99/1 dichloromethane/methanol mixture. After evaporation of the solvents, 250 mg (83%) of N-[4′(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-hydroxy-N-methylbenzamide are collected in the form of a white powder with a melting point of 110° C.

Workup

  1. customThe organic phase is separated out
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 99/1 dichloromethane/methanol mixture
  8. customAfter evaporation of the solvents, 250 mg (83%) of N-[4′(2,4-dioxothiazolidin-5-ylmethyl)-biphenyl-3-ylmethyl]-4-hydroxy-N-methylbenzamide
  9. customare collected in the form of a white powder with a melting point of 110° C.

Sources & evidence

ORD record
ord-20d981926b514d7093de8678e20ffa08
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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