Hydrochloric Acid → HCID 69921464, compound

HRID 1953049Notes

Reaction equation

HRID 1953049 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH2:11][C@@H:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][OH:14])[CH2:11][C@@H:10]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:27]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10839455HCID 10839455, compound

Product 1

HCID 69921464HCID 69921464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S,5R)-3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (2.0 g, 3.91 mmol) in tetrahydrofuran (45 mL) was cooled in an ice bath. Aqueous 0.5M HCl solution (7.8 mL, 3.9 mmol) was added and the resulting mixture was allowed to warm to room temperature while stirring overnight. After a total reaction time of 24 hours, saturated aqueous NaHCO3 solution was added. The mixture was extracted twice with diethyl ether and the combined organic phases were washed with brine, dried over MgSO4 and concentrated to an oil. The title compound, a colorless oil (1.02 g, 65%), was isolated by flash chromatography on silica gel eluting with 50% ethyl acetate in hexane.

Workup

  1. extractionThe mixture was extracted twice with diethyl ether
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-38f847e0a99a46f4af6adc308d7d8c57
Source dataset
uspto-grants-2000_09
Patent number
US06114361

Reaction notes

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