Triphenylphosphine → (2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine

HRID 2371393ノート

反応式

HRID 2371393 の反応式
[CH3:1][N:2]1[CH2:6][C@H:5](O)[CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:42]([OH:45])(=[S:44])[CH3:43]>CN(C)C=O.ClCCl>[CH3:1][N:2]1[CH2:6][C@@H:5]([S:44][C:42](=[O:45])[CH3:43])[CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10920632(2S,4R)-4-Hydroxy-1-methylpyrrolidine-2-carboxamideHCID 178418634HCID 178418634、化合物

生成物 1

HCID 56626958(2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

(2S,4R)-1-Methyl-2-aminocarbonyl-4-hydroxypyrrolidine (540 mg) was dissolved in dry dimethylformamide (10 ml), and triphenylphosphine (1.78 g) was added thereto. To the resultant mixture, diethyl azodicarboxylate (1.07 ml) was added under nitrogen steam while ice-cooling, and the mixture was stirred for 35 minutes. Thioacetic acid (0.76 ml) was added to the mixture under ice-cooling, and stirring was continued for 30 minutes under ice-cooling and at room temperature for 4 hours. The reaction mixture was diluted with dichloromethane, washed with aqueous sodium bicarbonate solution and dried over magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give (2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine.

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitwas continued for 30 minutes under ice-
  5. washwashed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-917ff102df054d88b194bdc8918e6ac5
出典データセット
uspto-grants-1992_03
特許番号
US05093328

反応ノート

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