Water → HCID 86598806, compound

HRID 1174180Notes

Reaction equation

HRID 1174180 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][NH:6][C@@H:7]([C@@H:15]([CH3:18])[CH2:16][CH3:17])[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@@H:15]([CH3:18])[CH2:16][CH3:17])[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[O:26]

Participants

5

Reactant 3

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 54030946tert-butyl(2S,3S)-2-[(2-ethoxy-2-oxoethyl)amino]-3-methylpentanoate

Product 1

HCID 86598806HCID 86598806, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution containing the product from Example 36A (5.7 g, 20.9 mmol) in dichloromethane (60 mL) at 0° C. was treated with chlorosulfonyl isocyanate (2.7 mL, 31.0 mmol) and the mixture was stirred at 0° C. for 16 hours. Water (60 mL) was added to the cold reaction and the mixture was warmed to 25° C. and stirred for 4 hours. The reaction 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 (6.83 g), which was used without further purification.

Workup

  1. temperaturethe mixture was warmed to 25° C.
  2. stirringstirred for 4 hours
  3. customThe reaction 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-d4e4cb0437984bcd9c55509998f3fc77
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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