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Sodium Hydroxide → 1-[2-(5-[1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]ethanol

HRID 1882063
Notes
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Reaction equation

HRID 1882063 reaction equation
[OH:1][CH:2]([C:4]1[S:8][C:7]([C:9](=O)[CH2:10][CH2:11][C:12](=O)[CH:13]([C:21]2[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=2)[CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[N:6][CH:5]=1)[CH3:3].C([O-])(=O)C.[NH4+:37].[OH-].[Na+]>C(O)(=O)C>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH:13]([C:12]2[NH:37][C:9]([C:7]3[S:8][C:4]([CH:2]([OH:1])[CH3:3])=[CH:5][N:6]=3)=[CH:10][CH:11]=2)[CH2:14][CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[CH:22][CH:23]=1)(=[O:28])=[O:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 593315121-[5-(1-hydroxyethyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 593315911-[2-(5-[1-[4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]ethanolYield 34.7%

Reagents, catalysts & solvents 1

HCID 176
Acetic Acid
Solvent

Conditions

Temperature
90 °C

Procedure

A mixture of 1-[5-(1-hydroxyethyl)-1,3-thiazol-2-yl]-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (0.57 g), ammonium acetate (0.46 g) and acetic acid (5 mL) was stirred at 90° C. for 3 hr. The reaction mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The ethyl acetate layer was concentrated, 2M aqueous sodium hydroxide solution (1 mL), tetrahydrofuran (4 mL) and methanol (4 mL) were added to the residue, and the mixture was stirred with heating under reflux for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to basic silica gel column chromatography, and the title compound (0.19 g, yield 34%) was obtained as a yellow amorphous solid from a fraction eluted with tetrahydrofuran-hexane (3:1, volume ratio). MS: 461 (MH+).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. addition2M aqueous sodium hydroxide solution (1 mL), tetrahydrofuran (4 mL) and methanol (4 mL) were added to the residue
  4. stirringthe mixture was stirred
  5. temperaturewith heating
  6. temperatureunder reflux for 2 hr
  7. additionWater was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with saturated brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-e6190db3790a40f2b17c34e29d6e31e0
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08318746B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes