Hydrochloric Acid → HCID 178450942, compound

HRID 852783Notes

Reaction equation

HRID 852783 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-2dbb7106e10e4bd2a45cc06d0fdd3337
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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