Water → HCID 21700057, compound

HRID 1597423Notes

Reaction equation

HRID 1597423 reaction equation
[OH:1][N:2]([CH:5]([C:26]1[CH:31]=[CH:30][C:29]([O:32]COC)=[CH:28][CH:27]=1)[CH2:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH:3]=[O:4].O>ClCCl>[OH:1][N:2]([CH:5]([C:26]1[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=1)[CH2:6][S:7]([C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=2)=[CH:14][CH:15]=1)(=[O:9])=[O:8])[CH:3]=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 21700279HCID 21700279, compound

Product 1

HCID 21700057HCID 21700057, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of Example 129 (186 mg, 0.366 mmol) in dichloromethane (20 mL) at −78° C. was treated with boranetrifluoride diethyl etherate (55.6 mL, 0.439 mmol), stirred at 0° C. for 3 hours and left at room temperature overnight, treated with water, extracted with ethyl acetate, dried (Na2SO4), filtered, concentrated and purified on silica gel with 80% ethyl acetate/hexanes to provide 45 mg (26%) of the title compound as an orange solid.

Workup

  1. waitleft at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel with 80% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4cabebf0fade48a583051a24f5f23516
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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