HCID 55295498, compound → HCID 118222051, compound

HRID 1754296Notes

Reaction equation

HRID 1754296 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][CH:16]1[CH2:18][CH2:17]1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].[O:19]1[CH2:25][CH:24]([OH:26])[CH2:23][NH:22][CH2:21][CH2:20]1>CC#N>[CH:16]1([O:15][C:14]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=2[S:2]([N:22]2[CH2:23][CH:24]([OH:26])[CH2:25][O:19][CH2:20][CH2:21]2)(=[O:4])=[O:3])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 55295498HCID 55295498, compoundHCID 118222071HCID 118222071, compound

Product 1

HCID 118222051HCID 118222051, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
28 °C

Procedure

To a solution of methyl 3-chlorosulfonyl-4-(cyclopropoxy)benzoate (840.00 mg, crude, 2.89 mmol, 1.00 eq) in MeCN (10.00 mL) were added 1,4-oxazepan-6-ol (338.49 mg, 2.89 mmol, 1.00 eq) and TEA (584.88 mg, 5.78 mmol, 2.00 eq). The resulting mixture was stirred at 28° C. until the starting material was consumed. The solvent was removed and the residue was purified by chromatography (silica gel, eluting with PE:EA=3:1) to give desired compound methyl 4-(cyclopropoxy)-3-[(6-hydroxy-1,4-oxazepan-4-yl)sulfonyl]benzoate (620.00 mg, 1.67 mmol, 57.76% yield) as white solid. LCMS: 372 [M+1].

Workup

  1. customwas consumed
  2. customThe solvent was removed
  3. customthe residue was purified by chromatography (silica gel, eluting with PE:EA=3:1)

Sources & evidence

ORD record
ord-9fa99982378d46b0bfcc70a477f0ae7f
Source dataset
uspto-grants-2015_10
Patent number
US09169212B2

Reaction notes

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