Sodium Hydroxide → HCID 178432838, compound

HRID 1893362Notes

Reaction equation

HRID 1893362 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[O:12][C:13]([Cl:17])=[C:14]([CH3:16])[N:15]=2)[CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>O1CCOCC1>[Cl:17][C:13]1[O:12][C:11]([C@H:8]2[CH2:7][CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9]2)=[N:15][C:14]=1[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178501059HCID 178501059, compound

Product 1

HCID 178432838HCID 178432838, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of trans-4-(5-chloro-4-methyl-oxazol-2-yl)-cyclohexanecarboxylic acid methyl ester (285 mg, 1.11 mmol) in 1,4-dioxane (5.5 ml) and 2 M aqueous sodium hydroxide solution (5.5 ml, 11 mmol) was stirred for 4 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 2. 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 10-ml portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound (245 mg, 91%) as white solid. MS m/e: 242 ([M−H]−)

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (25 ml) and water (25 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer 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-0d9c943f428e41049ae4cfe6eaa268d8
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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