Ammonium Chloride → Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

HRID 371279

反応式

HRID 371279 の反応式
[C:1]1([CH3:29])[C:2]([S:7]([O:10][C:11]2[CH2:17][CH:16]3[N:13]([C:14](=[O:18])[CH2:15]3)[C:12]=2[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.C([N-]C(C)C)(C)C.[Li+].[F:38][C:39]([F:43])([F:42])[CH:40]=[O:41].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[F:38][C:39]([F:43])([F:42])[CH:40]([CH:15]1[C:14](=[O:18])[N:13]2[CH:16]1[CH2:17][C:11]([O:10][S:7]([C:2]1[C:1]([CH3:29])=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:9])=[O:8])=[C:12]2[C:19]([O:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])[OH:41]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 65564TrifluoroacetaldehydeHCID 2724682Lithium diisopropylamideHCID 131712683Benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

生成物 1

HCID 131714283Benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

A solution of benzyl 3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate (41 mg) in anhydrous THF (0.5 ml) is added dropwise over 5 mins to a stirring solution of lithium diisopropylamide (from 15.5 μl of diisopropylamine and 70 μl of 1.6N BuLi) in anhydrous THF (1.5 ml) at -78°. The resulting solution is stirred under a N2 atm at -78° for 10 mins and then trifluoroacetaldehyde (50 mg) is added all at once. After 1 more min, saturated aqueous NH4Cl solution (1.5 ml) is added and the mixture is allowed to warm to room temperature. The mixture is diluted with EtOAc (20 ml), washed with water and brine, dried with MgSO4, filtered, and evaporated in vacuo. The benzyl 6-(2,2,2-trifluoro-1-hydroxyethyl)-3-toluenesulfonyloxy-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylate.

後処理

  1. washwashed with water and brine
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-111f03d423fb4d3d9a0c6e83c4fafd9e
出典データセット
uspto-grants-1985_07
特許番号
US04530841

関連ノート

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