Ammonia → 2-[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]acetamide

HRID 1888322Notes

Reaction equation

HRID 1888322 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17]([O:19]C)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH3:21]>CO>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]1[CH2:16][C:17]([NH2:21])=[O:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 56834436Methyl [(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]acetate

Product 1

HCID 668580382-[(2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-1-pyrrolidinyl]acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound 66 (13.7 g) in methanol (91 mL) was added 28% ammonia (91 mL) at room temperature and the solution was stirred overnight. The reaction solution was concentrated. Brine and ethyl acetate were added thereto and the solution was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=1:0→97:3→95:5→90:10) to give the title compound (10.1 g) having the following physical data.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionBrine and ethyl acetate were added
  3. customthe solution was separated
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate:methanol=1:0→97:3→95:5→90:10)

Sources & evidence

ORD record
ord-a3a43865a93247eba04c57b001404600
Source dataset
uspto-grants-2013_08
Patent number
US08501793B2

Reaction notes

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