Water → HCID 86709139, compound

HRID 931526Notes

Reaction equation

HRID 931526 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[O:8][C:9]=1[CH3:10].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].O>C(OCC)(=O)C>[CH3:28][S:29]([O:1][CH2:2][CH2:3][CH2:4][C:5]1[N:6]=[C:7]([C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)[O:8][C:9]=1[CH3:10])(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68278578HCID 68278578, compound

Product 1

HCID 86709139HCID 86709139, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-[4-(3-hydroxypropyl)-5-methyl-1,3-oxazol-2-yl]benzoate (500 mg, 1.82 mmol, 1.00 equiv) and triethylamine (370 mg, 3.66 mmol, 2.01 equiv) in ethyl acetate (20 mL) at −5° C. was added methanesulfonyl chloride (0.27 g) dropwise with stirring. The resulting solution was warmed to room temperature naturally and stirred at room temperature for 1 h. Water (20 mL) was added and the mixture was extracted with 1×30 mL of ethyl acetate. The organic layer was washed sequentially with 1×10 mL of 1 N hydrochloric acid, 1×10 mL of 5% sodium bicarbonate solution and 1×30 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 0.55 g (86%) of methyl 4-[4-[3-(methanesulfonyloxy)propyl]-5-methyl-1,3-oxazol-2-yl]benzoate as a white solid. LC-MS: (ES, m/z): 354 [M+H]+, 258, 146, 105.

Workup

  1. stirringstirred at room temperature for 1 h
  2. extractionthe mixture was extracted with 1×30 mL of ethyl acetate
  3. washThe organic layer was washed sequentially with 1×10 mL of 1 N hydrochloric acid, 1×10 mL of 5% sodium bicarbonate solution and 1×30 mL of brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2dfe8bd588804b7eb1b80c16ecca50b3
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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