Acetic Acid → 3-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891808ノート

反応式

HRID 891808 の反応式
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28](OC)=[O:29])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1.C[Al](C)C.C(O)(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:29])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8857Ethyl Acetate2 回HCID 222427783-t-Butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidineHCID 22243015Morpholine trimethylaluminium

生成物 1

HCID 222428193-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine収率 36%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (1.00 g, 2.29 mmol) (obtained as described in Reference Example 70(8)) in toluene (50 ml) was added a solution of 0.67 M morpholine-trimethylaluminium in toluene (6.87 ml) at room temperature under an atmosphere of nitrogen and the mixture was stirred in an oil bath (80° C.) for 4 hours. After checking the completion of the reaction, to the reaction mixture were added 10% aqueous acetic acid (50 ml) and ethyl acetate (100 ml) in an ice bath and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added ethyl acetate. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:2) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (400 mg, yield 36%) as a pale brown solid.

後処理

  1. customat room temperature
  2. customthe completion of the reaction
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. customThe mixture was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-f5f783da8328401f8b4e4f42d400284e
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

読み込み中…