Methanol → HCID 9968698, compound

HRID 1015617Notes

Reaction equation

HRID 1015617 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][C:9]=1[NH:10][C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:4].O1CCCC1.CO.[OH-].[Li+]>O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:11]([NH:10][C:9]2[CH:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[S:6][C:5]=2[C:3]([OH:4])=[O:2])=[O:19])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 20775759HCID 20775759, compound

Product 1

HCID 9968698HCID 9968698, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 3-(4-Chloro-benzoylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (30 mg, 0.081 mmol) in 1 ml of a 3:2:1 solution made with tetrahydrofuran, methanol and water respectively was added lithium hydroxide monohydrated (20 mg, 0.484 mmol). The mixture was stirred 30 minutes at 60 C, cooled to room temperature, diluted with water and washed with ether (2×). The collected aqueous layer was then acidified with KHSO4 20% to pH 3 and extracted with ethyl acetate (3×). The combined ethyl acetate layers were washed with brine, dried (Na2SO4) and concentrated. The resulting crude was taken in ethyl acetate and reexctracted with NaOH 0.5 N (2×). The combined aqueous layers were then back-washed with ethyl acetate and acidified to pH3 with KHSO4 20% and back-extracted with ethyl acetate (2×). The combined organic layers were washed with brine and dried (Na2SO4). 1H NMR (DMSO-d6, 400 MHz) 8.35 (s, 1H), 8.02-7.99 (m, 2H), 7.71-7.68 (m, 2H), 7.56-7.53 (m, 2H), 7.43-7.39 (m, 2H), 7.35-7.31 (m, 1H).

Workup

  1. washwashed with ether (2×)
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined ethyl acetate layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. washThe combined aqueous layers were then back-washed with ethyl acetate
  7. extractionback-extracted with ethyl acetate (2×)
  8. washThe combined organic layers were washed with brine
  9. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-6cecfc3c8b604ff493d83aef2f707979
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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