Hydrochloric Acid → Benzyl 2-chloro-6-fluoro-3-(propylsulfonamido)benzoate

HRID 1943855Notes

Reaction equation

HRID 1943855 reaction equation
[Cl:1][C:2]1[C:17]([N:18](S(CCC)(=O)=O)[S:19]([CH2:22][CH2:23][CH3:24])(=[O:21])=[O:20])=[CH:16][CH:15]=[C:14]([F:31])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].Cl.C(=O)(O)[O-].[Na+]>C1COCC1.[Li+].[OH-]>[Cl:1][C:2]1[C:17]([NH:18][S:19]([CH2:22][CH2:23][CH3:24])(=[O:20])=[O:21])=[CH:16][CH:15]=[C:14]([F:31])[C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 58095368benzyl chloro-6-fluoro-3-(N-(propylsulfonyl)propylsulfonamido)benzoate

Product 1

HCID 66840819Benzyl 2-chloro-6-fluoro-3-(propylsulfonamido)benzoateYield 53.9%

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 2-chloro-6-fluoro-3-(N-(propylsulfonyl) propylsulfonamido)benzoate (413.2 mg, 0.840 mmol) was dissolved in THF (8.4 mL) and 2.0M aqueous LiOH (1.26 mL). The mixture was refluxed for 16 hours and then allowed to cool to ambient temperature. The mixture was acidified to a pH of 0 with 1.0M HCl (5.0 mL) and then adjusted to a pH of 4 using saturated sodium bicarbonate. The mixture was extracted with EtOAc (2×). The extracts were washed with water (2×) and brine (1×), dried over sodium sulfate and concentrated to afford benzyl 2-chloro-6-fluoro-3-(propylsulfonamido)benzoate (174.5 mg, 0.4523 mmol, 53.9% yield). MS (APCI-neg) m/z=384.1 (M−H).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. extractionThe mixture was extracted with EtOAc (2×)
  3. washThe extracts were washed with water (2×) and brine (1×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-735e2ba1a858430fa932fb93541aad5c
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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