Sodium Hydroxide → HCID 178432840, compound

HRID 1893363Notes

Reaction equation

HRID 1893363 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]([Cl:18])=[C:15]([CH3:17])[N:16]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>O1CCOCC1>[Cl:18][C:14]1[S:13][C:12]([C@H:9]2[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[N:16][C:15]=1[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178472354HCID 178472354, compound

Product 1

HCID 178432840HCID 178432840, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of cis/trans-4-(5-chloro-4-methyl-thiazol-2-yl)-cyclohexanecarboxylic acid ethyl ester (1:5) (209 mg, 0.726 mmol) in 1,4-dioxane (7.3 ml) and 2 M aqueous sodium hydroxide solution (3.6 ml, 7.3 mmol) was stirred for 12 h at room temperature. The reaction mixture was partitioned between ethyl acetate (25 ml) and 0.1 M aqueous hydrogen chloride solution (25 ml). The layers were separated. The aqueous layer (pH 2) was extracted with two 25-ml portions of ethyl acetate. The combined organic layers were washed with one 10-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (170 mg, 90%) as white solid. MS m/e: 258 ([M−H]−)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (25 ml) and 0.1 M aqueous hydrogen chloride solution (25 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer (pH 2) was extracted with two 25-ml portions of ethyl acetate
  4. washThe combined organic layers were washed with one 10-ml portion of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b1c4d082c684daab060f46103dee49b
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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