Hydrochloric Acid → (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine

HRID 568262Notes

Reaction equation

HRID 568262 reaction equation
Cl.[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([O:23][Si](C(C)(C)C)(C)C)[CH2:9]1)=[O:7])[CH:3]=[CH2:4]>C(#N)C>[CH2:2]([O:5][C:6]([N:8]1[C@H:12]([CH:13]([OH:22])[C:14]2[N:15]3[CH:21]=[N:20][CH:19]=[C:16]3[S:17][CH:18]=2)[CH2:11][C@@H:10]([OH:23])[CH2:9]1)=[O:7])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 20639577HCID 20639577, compound

Product 1

HCID 70220671(3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidineYield 117.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
15 °C

Procedure

Concentrated hydrochloric acid (2.0 ml) is added dropwise to a solution of 525 mg of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer A) in 50 ml of dry acetonitrile under ice cooling (internal temperature 7° C.). The mixture is stirred in this state for 5 min, and the temperature is then raised to 15° C. over a period of 20 min. The reaction solution is concentrated to about 20 ml under reduced pressure, and the concentrate is adjusted to pH 8.5 by addition of 40 ml of a 5% aqueous sodium hydrogencarbonate solution. The mixture is then extracted three times with 100 ml of ethyl acetate. The combined organic layers are dried over magnesium sulfate, and the solvent is removed by evaporation under reduced pressure to give 457 mg of crude (3R,5S)-1-allyloxycarbonyl-3-hydroxy-5-[1-hydroxy-1-(imidazo[5,1-b]thiazol-3-yl)methyl]pyrrolidine (stereoisomer A) as a milky white amorphous material.

Workup

  1. concentrationThe reaction solution is concentrated to about 20 ml under reduced pressure
  2. additionthe concentrate is adjusted to pH 8.5 by addition of 40 ml of a 5% aqueous sodium hydrogencarbonate solution
  3. extractionThe mixture is then extracted three times with 100 ml of ethyl acetate
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fb5a17fe55554b299580a5cbfbf6f06d
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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