Hydrochloric Acid → HCID 70220637, compound

HRID 568292Notes

Reaction equation

HRID 568292 reaction equation
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[S:18][C:17]3=[CH:19][N:20]=[C:21]([S:22][CH3:23])[N:16]3[CH:15]=2)[CH2:11][C@@H:10]([O:24][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C(#N)C>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[S:18][C:17]3=[CH:19][N:20]=[C:21]([S:22][CH3:23])[N:16]3[CH:15]=2)[CH2:11][C@@H:10]([OH:24])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 20639585HCID 20639585, compound

Product 1

HCID 70220637HCID 70220637, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Concentrated hydrochloric acid (1.3 ml) is added to a solution of 1.37 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(5-methylthioimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine in 15 ml of acetonitrile under ice cooling, and the mixture is stirred for 30 min. The reaction mixture is neutralized with a saturated sodium hydrogencarbonate solution, and ethyl acetate is added, followed by extraction three times. The extract is washed three times with semi-saturated saline and dried over magnesium sulfate. The solvent is removed by evaporation to give 1.03 g of (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-(5-methylthioimidazo[5,1-b]thiazol-2-yl)methylpyrrolidine. This compound is dissolved in 18 ml of THF, 1.53 g of triphenylphosphine and 0.92 ml of diethyl azodicarboxylate are added thereto at −17° C., and the mixture is stirred for 30 min. Further, 0.7 ml of thiobenzoic acid is added thereto, and the mixture is stirred at about −20° C. for 40 min. The solvent is removed by evaporation, and the residue is purified by column chromatography on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 1.06 g of the title compound as a yellow oil.

Workup

  1. additionis added
  2. extractionfollowed by extraction three times
  3. washThe extract is washed three times with semi-saturated saline
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed by evaporation

Sources & evidence

ORD record
ord-f772422cee274ef6ad8b1b55075bde87
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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