Hydrochloric Acid → HCID 178450942, compound

HRID 46121Notes

Reaction equation

HRID 46121 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1(C(OCC)=O)[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])=[N:11][C:10]1=[O:25])([CH3:4])([CH3:3])[CH3:2].C1COCC1.O[Li].O.Cl>O.CO>[O:25]=[C:10]1[CH:9]([CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:31])[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:22])[F:23])=[N:11]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 178469100HCID 178469100, compound

Product 1

HCID 178450942HCID 178450942, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of ethyl 5-(3-tert-butoxy-3-oxopropyl)-4-oxo-2-(2-(trifluoromethyl)phenylamino)-4,5-dihydrothiazole-5-carboxylate (88.7 mg, 0.19 mmol), THF (1 mL), MeOH (0.3 mL), and water (0.3 mL) was added LiOH.H2O (Aldrich, 20 mg, 0.47 mmol) at room temperature. After 3 h, 1N HCl (0.7 mL) was added to the reaction mixture at 0° C. The mixture was extracted with EtOAc, and the organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography. MS: 389 (M+1).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e4a61817c9848778873f4bcf09d7d70
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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