Water → HCID 86755988, compound

HRID 279374Notes

Reaction equation

HRID 279374 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([O:16]C(OC)=O)[CH:14]=2)[C@H:9]([N:23]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([C:39]([F:42])([F:41])[F:40])[CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:8][C@@H:7]1[CH3:43])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:21][CH3:22])=[C:13]([OH:16])[CH:14]=2)[C@H:9]([N:23]([CH2:28][C:29]2[CH:34]=[C:33]([C:35]([F:36])([F:37])[F:38])[CH:32]=[C:31]([C:39]([F:41])([F:40])[F:42])[CH:30]=2)[C:24]([O:26][CH3:27])=[O:25])[CH2:8][C@@H:7]1[CH3:43])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 86755989HCID 86755989, compound

Product 1

HCID 86755988HCID 86755988, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-methoxy-7-methoxycarbonyloxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (5.0 g, 8.0 mmol) and potassium carbonate (2.2 g, 16 mmol) in methanol (45 mL) was stirred at room temperature. After 12 hours, water (100 mL) was added, and the volatiles were removed in vacuo. The mixture was then extracted with ethyl acetate (3×100 mL), the combined organic extracts were washed with saturated sodium bicarbonate solution (50 mL), dried over sodium sulfate, filtered and concentrated in vacuo to give 4.67 g of crude product. Purification by silica gel chromatography using 0-25% ethyl acetate/hexanes as eluent afforded 2.27 g of the title compound (50%). MS m/z 566 (M++2), 583 (M++19); 1H NMR (CDCl3) δ7.07 (C8, s, 1H), 6.36 (C5, s, 1H).

Workup

  1. customthe volatiles were removed in vacuo
  2. extractionThe mixture was then extracted with ethyl acetate (3×100 mL)
  3. washthe combined organic extracts were washed with saturated sodium bicarbonate solution (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give 4.67 g of crude product
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-edb86f2ad75a4d918124dff6748cac68
Source dataset
uspto-grants-2002_03
Patent number
US06362198B1

Reaction notes

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