Hydrochloric Acid → HCID 86690999, compound

HRID 70471Notes

Reaction equation

HRID 70471 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-c22d3ff431fb4bdaa41c0752e3257d2c
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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