Hydrochloric Acid → HCID 86690999, compound

HRID 520979Notes

Reaction equation

HRID 520979 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([O:13]C)=[O:12])=[C:4]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[F:26])(=[O:18])=[O:17])[CH:3]=1.O[Li].O.Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[C:4]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[F:26])(=[O:18])=[O:17])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86690997HCID 86690997, compound

Product 1

HCID 86690999HCID 86690999, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(4-chloro-2-{[(4-chloro-2-fluorophenyl)sulfonyl]amino}phenyl)sulfanyl]propanoate (545 mg, 1.24 mmol) in THF (10 ml) was added a solution of LiOH.H2O (104 mg, 2.48 mmol) in H2O (2 ml). The reaction was stirred at room temperature for 1.5 hours, acidified with 1M HCl, and was extracted with EtOAc (×2). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated. The crude product was triturated with CH2Cl2, filtered, rinsed with H2O, and dried to yield the title compound as beige solid (500 mg, 95%).

Workup

  1. extractionwas extracted with EtOAc (×2)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was triturated with CH2Cl2
  6. filtrationfiltered
  7. washrinsed with H2O
  8. customdried

Sources & evidence

ORD record
ord-62299a27e0cd4567a5705f0ce3417d92
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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