Hydrochloric Acid → HCID 70220620, compound

HRID 568280Notes

Reaction equation

HRID 568280 reaction equation
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[N:15]=[CH:16][N:17]3[CH:21]=[CH:20][S:19][C:18]=23)[CH2:11][C@@H:10]([O:22][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4].C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][C:14]2[N:15]=[CH:16][N:17]3[CH:21]=[CH:20][S:19][C:18]=23)[CH2:11][C@@H:10]([OH:22])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 20639567HCID 20639567, compound

Product 1

HCID 70220620HCID 70220620, compoundYield 107.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Concentrated hydrochloric acid (0.204 ml) is added dropwise to a solution of 206 mg of (3R,5R)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-(imidazo[5,1-b]thiazol-7-yl)methylpyrrolidine in 5 ml of dry acetonitrile under ice cooling, and the mixture is stirred at that temperature for 20 min. The reaction solution is diluted with 20 ml of ethyl acetate, saline is added to the diluted solution, the mixture is adjusted to pH 9 by addition of a saturated aqueous sodium hydrogencarbonate solution, and the mixture is extracted three times with ethyl acetate. 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 (chloroform:methanol=10:1) to give 162 mg of (3R,5R)-1-allyloxycarbonyl-3-hydroxy-5-(imidazo[5,1-b]thiazol-7-yl)methylpyrrolidine.

Workup

  1. additionis added to the diluted solution
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent is removed by evaporation under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-38a8cca9b347439f97beddcceb967660
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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