Triphenylphosphine → HCID 86756318, compound

HRID 568270Notes

Reaction equation

HRID 568270 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH2:24][C:25]2[N:32]3[C:28]([S:29][CH:30]=[CH:31]3)=[CH:27][N:26]=2)[CH2:22][C@@H:21](O)[CH2:20]1)=[O:18])[CH:14]=[CH2:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:53]([OH:61])(=[S:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C1COCC1>[CH2:13]([O:16][C:17]([N:19]1[C@H:23]([CH2:24][C:25]2[N:32]3[C:28]([S:29][CH:30]=[CH:31]3)=[CH:27][N:26]=2)[CH2:22][C@H:21]([S:60][C:53](=[O:61])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:20]1)=[O:18])[CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70220435HCID 70220435, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 86756318HCID 86756318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.105 ml) is added to a solution of 102 mg of (3R,5R)-1-allyloxycarbonyl-3-hydroxy-5-(imidazo[5,1-b]thiazol-5-yl)methylpyrrolidine and 174 mg of triphenylphosphine in 1.7 ml of anhydrous THF at −11 to −10° C., the mixture is stirred in this state for 15 min, 0.130 ml of thiobenzoic acid (90%) is added thereto, and the mixture is stirred for 14 hr while raising the temperature this state to room temperature. The solvent and the excess reagent are removed by evaporation under reduced pressure to give a yellow oil which is then successively purified by column chromatography on Sephadex LH-20 (chloroform:methanol=1:1) and on silica gel (first, n-hexane:ethyl acetate=1:1) to give 87 mg of the title compound as a yellow oil.

Workup

  1. stirringthe mixture is stirred for 14 hr
  2. customThe solvent and the excess reagent are removed by evaporation under reduced pressure
  3. customto give a yellow oil which
  4. customis then successively purified by column chromatography on Sephadex

Sources & evidence

ORD record
ord-dde87a2481574256b5233b7607d148d1
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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