Triethylamine → 4-(3-Benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one

HRID 247483ノート

反応式

HRID 247483 の反応式
C(C1C=CC(S([N:13]=[N+:14]=[N-])(=O)=O)=CC=1)(O)=O.[CH2:16]([O:23][C:24]([CH2:26][C:27](=[O:34])[CH2:28][CH:29]1[NH:32][C:31](=[O:33])[CH2:30]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCN(CC)CC>C(#N)C.CCOC(C)=O>[CH2:16]([O:23][C:24]([C:26](=[N+:13]=[N-:14])[C:27](=[O:34])[CH2:28][CH:29]1[NH:32][C:31](=[O:33])[CH2:30]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 86999Benzoic acid, 4-(azidosulfonyl)-HCID 127954624-(3-Benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

生成物 1

HCID 543896694-(3-Benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one収率 74.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Freshly recrystallized p-carboxy benzene sulfonylazide (241 mg, 1.06 mmol) is added to a solution of 4-(3-benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one (276 mg, 1.06 mmol) in anhydrous acetonitrile (6.6 ml). The resulting suspension is cooled in an ice-bath and stirred while Et3N (443 μl, 3.18 mmol) is added. The resulting yellow solution is stirred at room temperature. A precipitate forms quickly. After 90 mins, the mixture is diluted with EtOAc (50 ml) and filtered. The filtrate is washed with H2O (2×10 ml), 0.5N NaOH (2×10 ml), H2O (4×10 ml) and brine, dried with MgSO4, filtered, and evaporated i.v. to an off-white solid (273 mg). This is triturated with Et2O to provide 4-(3-benzyloxycarbonyl-3-diazo-2-oxopropyl)-azetidin-2-one (227 mg) as a cream colored powder: ir (film from CHCl3) 3.0, 4.65, 5.66, 5.82, 6.05, 7.21, 7.70 and 8.23 cm-1 ; nmr (CDCl3) δ2.63 (ddd, 1), 2.97 (dd, 1), 3.15 (ddd, 1), 3.40 (dd, 1), 3.98 (m, 1), 5.27 (s, 2), 6.13 (m, 1), and 7.38 (s, 5); mass spectrum m/e 259, 245, 231, and 218.

後処理

  1. temperatureThe resulting suspension is cooled in an ice-bath
  2. additionis added
  3. filtrationfiltered
  4. washThe filtrate is washed with H2O (2×10 ml), 0.5N NaOH (2×10 ml), H2O (4×10 ml) and brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporated i.v
  8. customThis is triturated with Et2O

出典と根拠

ORDレコード
ord-60050fafb4794172ad3596dc8a296370
出典データセット
uspto-grants-1987_11
特許番号
US04707547

反応ノート

読み込み中…