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Triphenylphosphine → (3S,5S)-1-Allyloxycarbonyl-3-benzoylthio-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine

HRID 568297
ノート
印刷プレビュー

反応式

HRID 568297 の反応式
[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[S:17][C:16]3=[CH:18][N:19]=[C:20]([Cl:21])[N:15]3[CH:14]=2)[CH2:10][C@@H:9](O)[CH2:8]1)=[O:6])[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:54]([OH:62])(=[S:61])[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>C1COCC1>[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[S:17][C:16]3=[CH:18][N:19]=[C:20]([Cl:21])[N:15]3[CH:14]=2)[CH2:10][C@H:9]([S:61][C:54](=[O:62])[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 20639586(3R,5S)-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methyl-3-hydroxypyrrolidineHCID 178526132HCID 178526132、化合物

生成物 1

HCID 86756332(3S,5S)-1-Allyloxycarbonyl-3-benzoylthio-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 438 mg of (3R,5S)-1-allyloxycarbonyl-5-(5-chloroimidazo[5,1-b]thiazol-2-yl)methyl-3-hydroxypyrrolidine and 672 mg of triphenylphosphine in 6.5 ml of anhydrous THF is cooled to −10° C. in an argon atmosphere. Diethyl azodicarboxylate (0.40 ml) is added dropwise to the mixture over a period of 7 min while maintaining the solution at −5° C. or below, and the mixture is stirred in this state for 23 min. Thiobenzoic acid (90%) (0.34 ml) is added dropwise to the mixed solution at −10° C. over a period of 5 min, and the mixture is stirred in this state for additional 25 min. The solvent is removed by evaporation under reduced pressure to give an oil which is then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to give 505 mg of the title compound as a bright yellow viscous material.

後処理

  1. temperaturewhile maintaining the solution at −5° C. or below
  2. stirringthe mixture is stirred in this state for additional 25 min
  3. customThe solvent is removed by evaporation under reduced pressure
  4. customto give an oil which
  5. customis then purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-402ac52150754e0a8b6fcd4d22745cf5
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06180622B2

反応ノート

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