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Acetic Acid → 1-(4-p-Nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine

HRID 891549
ノート
印刷プレビュー

反応式

HRID 891549 の反応式
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=3)=[O:29])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N+:38]([C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:30][C:28]([C:26]2[N:27]=[C:23]([N:21]3[CH2:22][CH:19]([OH:18])[CH2:20]3)[S:24][CH:25]=2)=[O:29])=[CH:33][CH:34]=1)([O-:40])=[O:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 222427683-t-Butyldiphenylsilyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)azetidine

生成物 1

HCID 222428971-(4-p-Nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine収率 81%

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-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)azetidine (93 mg, 0.16 mmol) (obtained as described in Reference Example 2(5)) in anhydrous tetrahydrofuran (4.7 ml) were added acetic acid (0.028 ml, 0.49 mmol) and a solution of 1 M tetrabutylammonium fluoride in tetrahydrofuran (0.48 ml, 0.48 mmol) in an ice bath. The mixture was stirred for 2 hours. After checking the completion of the reaction, the reaction 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 toluene:acetonitrile (2:1) as the eluant to afford 1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (42.4 mg, yield 81%) as a pale yellow solid.

後処理

  1. customthe completion of the reaction
  2. customthe reaction 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-c7a39c70f409477c9b256c980aa1a7dc
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

読み込み中…

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