Hydrochloric Acid → HCID 58317006, compound

HRID 1187303Notes

Reaction equation

HRID 1187303 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])(=[O:13])=[O:12])[C:5]=1[F:22].[AlH4-].[Li+].[OH-].[Na+].Cl>O1CCCC1>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[S:11]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][OH:2])[C:5]=1[F:22])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28112Lithium aluminum hydrideHCID 583169963-(2,5-Difluoro-benzenesulfonylamino)-2-fluoro-benzoic acid methyl ester

Product 1

HCID 58317006HCID 58317006, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 3-(2,5-difluoro-benzenesulfonylamino)-2-fluoro-benzoic acid methyl ester (74, 0.955 g, 2.8 mmol) in 22 mL of tetrahydrofuran, lithium tetrahydroaluminate (6 mL, 1M in tetrahydrofuran, 6 mmol) is added at −40° C. under nitrogen. The reaction is allowed to warm to room temperature and stirred overnight. The reaction is poured into 1M aqueous sodium hydroxide, then neutralized with 1M aqueous hydrochloric acid. The solids are filtered through a bed of celite, and the celite bed is washed with ethyl acetate and tetrahydrofuran. The filtrate layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with brine, dried over sodium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (75, 0.875 g). MS (ESI) [M−H+]−=316.

Workup

  1. filtrationThe solids are filtered through a bed of celite
  2. washthe celite bed is washed with ethyl acetate and tetrahydrofuran
  3. customThe filtrate layers are separated
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate is concentrated under vacuum
  9. customThe resulting material is purified by silica gel column chromatography
  10. washeluting with ethyl acetate and dichloromethane
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-487fecff905d4b5aaf2d7b798fc26adb
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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