Tetraethyl orthocarbonate → HCID 68359207, compound

HRID 339880

Reaction equation

HRID 339880 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([F:17])([S:13]([NH2:16])(=[O:15])=[O:14])[C:9]([OH:12])([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([O:20][C:21](OCC)(OCC)OCC)[CH3:19]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([F:17])[C:9]([CH3:11])([CH3:10])[O:12][C:21]([O:20][CH2:18][CH3:19])=[N:16][S:13]2(=[O:14])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 66213Tetraethyl orthocarbonateHCID 68292393HCID 68292393, compound

Product 1

HCID 68359207HCID 68359207, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 75 mg of 1-(3-bromophenyl)-1-fluoro-2-hydroxy-2-methylpropane-1-sulfonamide in 5 ml of tetraethoxymethane and 1 ml of acetic acid was stirred at 100° C. for 1.5 hours. The conversion was checked by LCMS. Since it was incomplete, the reaction mixture was stirred at 100° C. for a further 3.5 hours. After the removal of the solvents under reduced pressure, the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (45.6 mg) with a molecular weight of 380.2 g/mol (C13H15BrFNO4S).

Workup

  1. stirringthe reaction mixture was stirred at 100° C. for a further 3.5 hours
  2. customAfter the removal of the solvents under reduced pressure
  3. customthe residue was purified by means of normal phase chromatography
  4. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-9bfd0b628c204c6d95b22f944706bc75
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Linked notes

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