Tetrabutylammonium Fluoride → 3-Hydroxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

HRID 891784ノート

反応式

HRID 891784 の反応式
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][NH:29][C:30]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[O:31])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][NH:29][C:30]([C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)=[O:31])[N:27]=2)[CH2:20]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 222428183-t-Butyldiphenylsilyloxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

生成物 1

HCID 222428533-Hydroxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine収率 47.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine (2.18 g, 4.08 mmol) (obtained as described in Reference Example 66(1)) in anhydrous tetrahydrofuran (110 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (4.90 ml, 4.90 mmol) in an ice bath and the mixture was stirred in an ice bath for 1 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 3-hydroxy-1-[4-(thiophene-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine (571 mg, yield 47%) as a white solid.

後処理

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

出典と根拠

ORDレコード
ord-063910bd263c4a20b6ff61cfb449c1bc
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…