Water → HCID 13825239, compound

HRID 2180225Notes

Reaction equation

HRID 2180225 reaction equation
[CH:1]1([CH2:7][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.O.OS([O-])(=O)=O.[K+]>CS(C)=O>[CH:1]1([CH2:7][C@@H:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 14014843HCID 14014843, compound

Product 1

HCID 13825239HCID 13825239, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of Example 1A (25.8 g,100 mmol), sulfur trioxide pyridine complex (79.6 g, 500 mmol), and triethylamine (69.7 mL, 500 mmol) in DMSO (70 mL) at room temperature was stirred for 30 minutes, cooled to 0° C., treated with water and saturated aqueous KHSO4, and extracted with ethyl acetate. The extract was washed with saturated aqueous KHSO4 and brine, dried (MgSO4), filtered, and concentrated to provide the desired product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous KHSO4 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-820f82ec53c8482583ca20af81093cf4
Source dataset
uspto-grants-2005_05
Patent number
US06887863B2

Reaction notes

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