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Toluene-p-sulphonic anhydride → Benzyl 3-(p-toluenesulfonyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 247493
ノート
印刷プレビュー

反応式

HRID 247493 の反応式
C1(C)C=CC(S([O:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])(=O)=O)=CC=1.C(N(CC)C(C)C)(C)C.[N:31]12[C:37](=[O:38])[CH2:36][CH:35]1[CH2:34][C:33](=O)[CH:32]2[C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)=[O:41]>C(Cl)Cl>[C:17]1([CH3:20])[CH:16]=[CH:15][C:14]([S:11]([O:10][C:33]2[CH2:34][CH:35]3[N:31]([C:37](=[O:38])[CH2:36]3)[C:32]=2[C:40]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[O:41])(=[O:12])=[O:13])=[CH:19][CH:18]=1
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 77773Toluene-p-sulphonic anhydrideHCID 81531DiisopropylethylamineHCID 12804725Benzyl 3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

生成物 1

HCID 12849001Benzyl 3-(p-toluenesulfonyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate収率 67%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

p-Toluenesulfonic anhydride (326 mg, 1 mμol) and N,N-diisopropylethylamine (192 μl, 1.1 mμol) are added to an ice-cold, stirring solution of benzyl 1-azabicyclo[3.2.0]heptan-3,7-dione-2-carboxylate (259 mg, 1 mμol) in anhydrous methylene chloride (10 ml). The resulting solution is stirred in the cold and under a nitrogen atmosphere for 2.5 hours. The solution is diluted with methylene chloride (20 ml), washed with water (10 ml), 1M pH3 phosphate buffer (10 ml) and 5% aqueous sodium bicarbonate (2×10 ml) dried with magnesium sulfate, filtered, and evaporated under vacuum to a semi-solid. This material is triturated with ice-cold ethyl acetate (2×2 ml) and diethyl ether (2×5 ml) to provide benzyl 3-(p-toluenesulfonyloxy)-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (276 mg, 67%) as a white powder. Recrystallization from methylene chloride-diethyl ether gives analytically pure product as small white needles: mp 103° -105°; IR (CH2Cl2) 1786, 1723, 1382, and 1190 cm-1 ; NMR (CDCl3) 8 2.44 (s, 3, ArCh3) 3.03 (dd, 1, J=3.0 and 17.0, HGβ), 3.16 (dd, 1, J=8.5 and 18.7, H4a), 3.32 (dd, 1, J=10.0 and 18.7, H46), 3.55 (dd, 1, J=5.5 and 17.0, HG), 4.21 (m, 1, H5), 5.14 (ABq, 2, J=12, CH2Ar), 7.35 (S, 5, ArH0, 7.26 and 7.75 (two d's, 4, J=9, ArH); UV(dioxane) 283 (E6600) and 277 (E6500) nm.

後処理

  1. washwashed with water (10 ml), 1M pH3 phosphate buffer (10 ml) and 5% aqueous sodium bicarbonate (2×10 ml)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under vacuum to a semi-solid
  5. customThis material is triturated with ice-cold ethyl acetate (2×2 ml) and diethyl ether (2×5 ml)

出典と根拠

ORDレコード
ord-08220200179140bd9030226b6c4b6c06
出典データセット
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04707547

反応ノート

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