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

HRID 2371393노트

반응식

HRID 2371393 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-917ff102df054d88b194bdc8918e6ac5
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093328

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