Water → tert-butyl(2S)-2-[(aminocarbonyl)(2-ethoxy-2-oxoethyl)amino]-3,3-dimethylbutanoate

HRID 1174190Notes

Reaction equation

HRID 1174190 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][C@@H:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH3:2].ClS([N:24]=[C:25]=[O:26])(=O)=O.O>ClCCl>[NH2:24][C:25]([N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:19])[C@@H:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 86598807tert-butyl(2S)-2-[(2-ethoxy-2-oxoethyl)amino]-3,3-dimethylbutanoate

Product 1

HCID 86598808tert-butyl(2S)-2-[(aminocarbonyl)(2-ethoxy-2-oxoethyl)amino]-3,3-dimethylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing the product from Example 46A (5.74 g, 20.0 mmol) in dichloromethane (40 mL) at 0° C. was treated with chlorosulfonyl isocyanate (2.26 mL, 26.0 mmol) and the mixture was stirred at 0° C. for 2 hours. Water (40 mL) was added to the cold reaction and the mixture was warmed to 25° C. and stirred for 2 hours. The reaction mixture was partitioned between dichloromethane and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound, which was used without further purification.

Workup

  1. temperaturethe mixture was warmed to 25° C.
  2. stirringstirred for 2 hours
  3. customThe reaction mixture was partitioned between dichloromethane and water
  4. washthe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7790eb316e1a4eddbd3eb01290dc394b
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…