Hydrochloric Acid → HCID 71714788, compound

HRID 70469Notes

Reaction equation

HRID 70469 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][CH2:22][CH2:23][C:24]([O:26]C)=[O:25])(=[O:12])=[O:11].O[Li].O.Cl>C1COCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:11])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 71714789HCID 71714789, compound

Product 1

HCID 71714788HCID 71714788, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)propanoate (125 mg, 0.29 mmol) in THF (3 ml) was added a solution of LiOH.H2O (25 mg, 0.59 mmol) in H2O (1 ml). The reaction was stirred at room temperature for 1 hour, acidified with 1M HCl, and was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was triturated with MeOH to yield the title compound (102 mg, 84%).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with MeOH

Sources & evidence

ORD record
ord-c7a618bede1b4ab7943df90ccb052f4e
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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