HCID 58706768, compound → HCID 58706673, compound

HRID 1716514Notes

Reaction equation

HRID 1716514 reaction equation
C(OC([N:8]1[C@H:12]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]4[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=4)[N:19]=3)=[CH:16][N:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C>O1CCCC1.C(OCC)(=O)C.Cl>[NH2:8][C@H:12]([C:13]1[S:14][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]3[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][N:26]=3)[N:19]=2)=[CH:16][N:17]=1)[CH2:11][OH:10]

Participants

4

Reactant 1

HCID 58706768HCID 58706768, compound

Product 1

HCID 58706673HCID 58706673, compoundYield 44.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2,2-dimethyl-4-{5-[6-(4-methylpyridin-2-ylamino)pyridin-2-yl]thiazol-2-yl}oxazolidine-3-carboxylic acid tert-butyl ester (1.90 g, 4.06 mmol) obtained in Example 12 in tetrahydrofuran (10 ml), 4N hydrogen chloride-ethyl acetate solution (10 ml) was added and stirred at 60° C. for 5 hours. After the reaction solution was concentrated, it was neutralized with a saturated aqeous sodium bicarbonate, and extracted with ethyl acetate. After the organic layer was washed with a saturated brine and dried over magnesium sulfate, it was concentrated and the residue was purified by flash chromatography on silica gel (chloroform:methanol=20:1) and the title compound (588 mg, 44%) was obtained.

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. extractionextracted with ethyl acetate
  3. washAfter the organic layer was washed with a saturated brine
  4. dry with materialdried over magnesium sulfate, it
  5. concentrationwas concentrated
  6. customthe residue was purified by flash chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-35f71197ff48468fb0a8707eacd249eb
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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