Triphenylphosphine → HCID 86756324, compound

HRID 568281Notes

Reaction equation

HRID 568281 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[N:14]=[CH:15][N:16]3[CH:20]=[CH:19][S:18][C:17]=23)[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:53]([OH:61])(=[S:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[C@H:11]([CH2:12][C:13]2[N:14]=[CH:15][N:16]3[CH:20]=[CH:19][S:18][C:17]=23)[CH2:10][C@H:9]([S:60][C:53](=[O:61])[C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium BicarbonateHCID 70220620HCID 70220620, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 86756324HCID 86756324, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 134 mg of (3R,5R)-1-allyloxycarbonyl-3-hydroxy-5-(imidazo[5,1-b]thiazol-7-yl)methylpyrrolidine in 8 ml of THF is ice-cooled. Triphenylphosphine (228 mg) and 0.139 ml of diethyl azodicarboxylate are added in an argon atmosphere. The mixture is stirred at that temperature for 1.5 hr, 0.104 ml of thiobenzoic acid is added thereto, and the mixture is stirred at that temperature for 20 min and then at room temperature for 3 hr. The reaction solution is diluted with 30 ml of ethyl acetate, saline is added thereto, the mixture is adjusted to pH 9 by addition of a saturated aqueous sodium hydrogencarbonate solution, and the organic layer is separated. The organic layer is dried over anhydrous magnesium sulfate and filtered, and the solvent is removed by evaporation under reduced pressure. The residue is purified by column chromatography on silica gel (toluene:ethyl acetate=1:1→chloroform:ethyl acetate 2:1) to give 147 mg of the title compound.

Workup

  1. temperaturecooled
  2. stirringthe mixture is stirred at that temperature for 20 min
  3. waitat room temperature for 3 hr
  4. additionis added
  5. customthe organic layer is separated
  6. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed by evaporation under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel (toluene:ethyl acetate=1:1→chloroform:ethyl acetate 2:1)

Sources & evidence

ORD record
ord-141491d986514f39987ca659f2c70291
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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