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Imidazole → 3-t-Butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891805
ノート
印刷プレビュー

反応式

HRID 891805 の反応式
[OH:1][CH:2]1[CH2:5][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=2)[CH2:3]1.[C:15]([SiH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16].N1C=CN=C1.CO>CN(C)C=O>[Si:19]([O:1][CH:2]1[CH2:5][N:4]([C:6]2[O:7][CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[N:10]=2)[CH2:3]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 795ImidazoleHCID 887MethanolHCID 222430383-Hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidineHCID 57348992tert-Butyl(diphenyl)silane

生成物 1

HCID 222427783-t-Butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine収率 85%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of 3-hydroxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (2.64 g, 13.4 mmol) (obtained as described in Reference Example 70(7)) in dimethylformamide (80 ml) were added t-butyldiphenylsilane (6.97 ml, 26.8 mmol) and imidazole (1.82 g, 26.8 mmol) in an ice bath and the mixture was stirred in an ice bath overnight. After checking the completion of the reaction, methanol was added to the reaction mixture and the mixture was stirred for 30 minutes. The resulting mixture was partitioned between ethyl acetate and 1 0% aqueous sodium chloride solution. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution 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 (4:3→3:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-methoxycarbonyl-1,3-oxazol-2-yl)azetidine (4.95 g, yield 85%) as a pale yellow solid.

後処理

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe resulting mixture was partitioned between ethyl acetate and 1 0% aqueous sodium chloride solution
  4. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-6d866d91550349b48467b800168d4acf
出典データセット
uspto-grants-2006_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07001897B2

反応ノート

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