Hydrochloric Acid → Benzyl 2-methyl-1-oxo-1-(2-oxoethylamino)propan-2-ylcarbamate

HRID 927347Notes

Reaction equation

HRID 927347 reaction equation
C[O:2][CH:3](OC)[CH2:4][NH:5][C:6](=[O:21])[C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:9])[CH3:8].Cl.C(OCC)(=O)C>C1COCC1>[CH3:9][C:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:8])[C:6](=[O:21])[NH:5][CH2:4][CH:3]=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86674736Benzyl 1-(2,2-dimethoxyethylamino)-2-methyl-1-oxopropan-2-ylcarbamate

Product 1

HCID 86674737Benzyl 2-methyl-1-oxo-1-(2-oxoethylamino)propan-2-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl 1-(2,2-dimethoxyethylamino)-2-methyl-1-oxopropan-2-ylcarbamate (0.52 g, 1.6 mmol) in THF (20 mL) was added 5 M hydrochloric acid (10 mL) and the mixture was stirred at room temperature until TLC showed the reaction was completed. Ethyl acetate (50 mL) was added and the phases were separated. The organic layer was washed with brine (4×30 mL) to pH=6-7, dried over anhydrous sodium sulfate and concentrated to yield product (0.445 g, 100%) as yellow oil, which was used directly in the next step without purification; MS: m/e 279.1 [M+H]+.

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with brine (4×30 mL) to pH=6-7
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a2f8677c609d4b2f9189c6fbb0a24423
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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