Diisopropylethylamine → N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide

HRID 56508

反応式

HRID 56508 の反応式
[CH3:1][O:2][CH:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH3:18])=[N:16][N:17]=2)=[CH:9][CH:8]=1)[C:4]([OH:6])=O.C([N:22]([CH:25](C)C)CC)(C)C.[CH3:28][O:29]CCN(S(F)(F)F)CCOC>C(Cl)Cl>[CH3:28][O:29][N:22]([CH3:25])[C:4](=[O:6])[CH:3]([O:2][CH3:1])[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[O:14][C:15]([CH3:18])=[N:16][N:17]=2)=[CH:9][CH:8]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 584320102-Methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid

生成物 1

HCID 58432086N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide収率 26%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice-cold solution of 2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid (6.8 g, 27.4 mmol) in anhydrous CH2Cl2 (270 mL) and diisopropylethylamine (17 mL, 97 mmol) under argon was added bis(2-methoxyethyl)aminosulfur trifluoride (5.6 mL, 30.3 mmol) dropwise. After stirring over an ice bath for 45 min, N,0-dimethylhydroxylamine hydrochloride (3.40 g, 34.8 mmol) was added in three aliquots over a period of 15 min. The mixture was stirred for 15 min then the ice bath was removed. After 3 hrs, saturated aqueous NaHCO3 was added and stirred for 30 min. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organics were washed with saturated aqueous NaHCO3, H2O and brine, dried over MgSO4, filtered through Celite and concentrated in vacuo. Purification by chromatography (75-100% EtOAc-hexanes then 0-5% EtOH-EtOAc) gave N,2-dimethoxy-N-methyl-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetamide as an oil that solidified upon standing (2.06 g, 26% yield).

後処理

  1. stirringThe mixture was stirred for 15 min
  2. customthe ice bath was removed
  3. waitAfter 3 hrs
  4. additionsaturated aqueous NaHCO3 was added
  5. stirringstirred for 30 min
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with CH2Cl2
  8. washThe combined organics were washed with saturated aqueous NaHCO3, H2O and brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered through Celite
  11. concentrationconcentrated in vacuo
  12. customPurification by chromatography (75-100% EtOAc-hexanes

出典と根拠

ORDレコード
ord-ee02eecf1aa14393aa6eaca46688aeac
出典データセット
uspto-grants-2016_09
特許番号
US09434707B2

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