Water → 2-Methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid

HRID 15096

反応式

HRID 15096 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:8]=1[C:9]([O:11]C(C)(C)C)=[O:10].[H-].[Na+].[CH3:23][C:24]1[O:28][C:27]([C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)=[N:26][C:25]=1[CH2:36]I.O>CC(OC)(C)C>[CH3:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:7]([CH2:6][O:5][CH2:4][CH2:3][CH2:2][O:1][CH2:36][C:25]2[N:26]=[C:27]([C:29]3[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)[O:28][C:24]=2[CH3:23])[C:8]=1[C:9]([OH:11])=[O:10]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 219803084-Iodomethyl-5-methyl-2-m-tolyloxazoleHCID 59341259Tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate

生成物 1

HCID 119907232-Methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid

試薬・触媒・溶媒 1

HCID 15413tert-Butyl methyl ether溶媒

実験手順

200 mg of tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate are dissolved in 1.0 ml of MTBE, and 57 mg of sodium hydride (60% in mineral oil) are added. After gas evolution ceases, 446 mg of 5-methyl-2-m-tolyloxazol-4-ylmethyl iodide are added, and the suspension is stirred at RT overnight. Water is then added, and the solution is poured into a kieselguhr cartridge (VARIAN CHEM ELUT 1010). The product is eluted with MTBE and concentrated. The residue is dissolved without purification in DCM/TFA (3:1) and stirred at 40° C. for 5 h. The solution is concentrated and purified by prep. HPLC, resulting in 202 mg of 2-methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid.

後処理

  1. additionthe solution is poured into a kieselguhr cartridge (VARIAN CHEM ELUT 1010)
  2. washThe product is eluted with MTBE
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved without purification in DCM/TFA (3:1)
  5. stirringstirred at 40° C. for 5 h
  6. concentrationThe solution is concentrated
  7. custompurified by prep
  8. customHPLC, resulting in 202 mg of 2-methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid

出典と根拠

ORDレコード
ord-263c2656eec34944ab4338ccd0d445ca
出典データセット
uspto-grants-2010_06
特許番号
US07732471B2

関連ノート

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