Sodium Hydroxide → HCID 178432839, compound

HRID 1893364Notes

Reaction equation

HRID 1893364 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[S:13][C:14]([CH3:18])=[C:15]([CH3:17])[N:16]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[CH3:17][C:15]1[N:16]=[C:12]([C@H:9]2[CH2:10][CH2:11][C@H:6]([C:4]([OH:5])=[O:3])[CH2:7][CH2:8]2)[S:13][C:14]=1[CH3:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472355HCID 178472355, compound

Product 1

HCID 178432839HCID 178432839, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of cis/trans-4-(4,5-dimethyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:7) (170 mg, 0.636 mmol) in 1,4-dioxane (6.4 ml) and 2 M aqueous sodium hydroxide solution (3.2 ml, 6.4 mmol) was stirred for 24 h at room temperature. The reaction mixture was partitioned between ethyl acetate (25 ml) and water (25 ml). The aqueous layer was acidified to pH 4-5 by addition of 2 M aqueous hydrogen chloride solution (3.2 ml). The layers were separated. The aqueous layer was extracted with two 25-ml portions of ethyl acetate. The combined organic layers were washed with one 20-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (136 mg, 89%) as white solid. MS m/e: 240 ([M−H]−)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (25 ml) and water (25 ml)
  2. additionThe aqueous layer was acidified to pH 4-5 by addition of 2 M aqueous hydrogen chloride solution (3.2 ml)
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with two 25-ml portions of ethyl acetate
  5. washThe combined organic layers were washed with one 20-ml portion of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c13c051e65a0428da63473e6c2e0e5a9
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

Loading…