Ethanol → HCID 59331418, compound

HRID 1882052Notes

Reaction equation

HRID 1882052 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27]C(CC#N)=C[N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3CCO[CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[OH-:34].[Na+].[O:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.[CH2:41]([OH:43])[CH3:42]>O>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:38]([CH2:39][C:40]([OH:36])=[O:34])=[CH:37][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:43][CH2:41][CH2:42]3)=[CH:11][CH:12]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59331242HCID 59331242, compound

Product 1

HCID 59331418HCID 59331418, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of [2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]acetonitrile (0.23 g), 2M aqueous sodium hydroxide solution (0.50 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) was stirred with heating under reflux for 6 hr. Water was added to the reaction mixture, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with 10% aqueous citric acid solution, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residual solid was dissolved in tetrahydrofuran, and the solution was treated with activated carbon and concentrated. The obtained solid was washed with cold ethyl acetate and dried to give the title compound (0.14 g, yield 58%) as colorless crystals. melting point 246-247° C. (decomposition). MS: 501 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 hr
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. dissolutionThe residual solid was dissolved in tetrahydrofuran
  9. additionthe solution was treated with activated carbon
  10. concentrationconcentrated
  11. washThe obtained solid was washed with cold ethyl acetate
  12. customdried

Sources & evidence

ORD record
ord-d75e2b59925445dfb5392abed90a2ce0
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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