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

HRID 568297Notes

Reaction equation

HRID 568297 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-402ac52150754e0a8b6fcd4d22745cf5
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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