Methylamine → tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate

HRID 1350196ノート

反応式

HRID 1350196 の反応式
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:36][NH2:37]>C1COCC1.CCOC(C)=O>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][NH:37][CH3:36])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

5

反応物 2

HCID 6329MethylamineHCID 16747945tert-Butyl (3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)1,2,4-oxadiazol-5-yl]hexanoate

生成物 1

HCID 16747948tert-butyl(3R)-6-cyclohexyl-3-{3-[(methylamino)methyl]-1,2,4-oxadiazol-5-yl}hexanoate収率 95%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

A solution of tert-butyl(3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,2,4-oxadiazol-5-yl]hexanoate (preparation 177) (492 mg, 0.97 mmol) in THF (1 ml) was treated with a solution of 2M methylamine in THF (7 ml, 14.4 mmol) and stirred at 40° C. in a sealed vessel for 75 minutes. The reaction mixture was allowed to cool to room temprature and dissolved in EtOAc (100 ml) which was washed with sat. NaHCO3 (100 ml) solution followed by brine. The organic extract was dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford the title compound as a colourless oil (337 mg, 95%).

後処理

  1. temperatureto cool to room temprature
  2. washwas washed with sat. NaHCO3 (100 ml) solution
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-b24ceadb3513407eb6bfd9ac78154de6
出典データセット
uspto-grants-2007_05
特許番号
US07214694B2

反応ノート

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