Methanol → HCID 9968698, compound

HRID 2193901Notes

Reaction equation

HRID 2193901 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×

Conditions

Temperature
60 °C

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

Sources & evidence

ORD record
ord-a498c1006b4b4cdd86f81ac63b2c4f30
Source dataset
uspto-grants-2012_12
Patent number
US08329924B2

Reaction notes

Loading…