Ethyl Acetate → (2R,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyridin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid 2-carboxy-2-methyl-propyl ester

HRID 661456Notes

Reaction equation

HRID 661456 reaction equation
C([O:5][C:6]([C:8]([CH3:58])([CH3:57])[CH2:9][O:10][C:11]([N:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([F:26])([F:25])[F:24])=[CH:20][CH:21]=2)[C@@H:16]([N:27]([CH2:40][C:41]2[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[C:43]([C:51]([F:54])([F:53])[F:52])[CH:42]=2)[C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:30][N:29]=2)[CH2:15][C@H:14]1[CH2:55][CH3:56])=[O:12])=[O:7])(C)(C)C.C(=O)([O-])O.[Na+].C(OCC)(=O)C>Cl.O1CCOCC1>[C:6]([C:8]([CH3:57])([CH3:58])[CH2:9][O:10][C:11]([N:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([F:25])([F:26])[F:24])=[CH:20][CH:21]=2)[C@@H:16]([N:27]([CH2:40][C:41]2[CH:46]=[C:45]([C:47]([F:48])([F:49])[F:50])[CH:44]=[C:43]([C:51]([F:54])([F:53])[F:52])[CH:42]=2)[C:28]2[CH:33]=[CH:32][C:31]([N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:30][N:29]=2)[CH2:15][C@H:14]1[CH2:55][CH3:56])=[O:12])([OH:7])=[O:5]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86636544(2R,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyridin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid 2-tert-butoxycarbonyl-2-methyl-propyl ester

Product 1

HCID 11693460(2R,4S)-4-[(3,5-Bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyridin-2-yl)-amino]-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid 2-carboxy-2-methyl-propyl ester

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

The compound obtained in Example 10 above (178 mg) was dissolved in 4N—HCl/dioxane (2 ml) and stirred at room temperature for 2.5 hours. To the reaction mixture, were added a saturated sodium hydrogen carbonate aq. solution and ethyl acetate and the organic layer was separated, washed with a saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel; chloroform:methanol=1:0→9:1) to give the titled compound (157 mg). MS (m/z): 777 [M+H]+.

Workup

  1. customthe organic layer was separated
  2. washwashed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica gel; chloroform:methanol=1:0→9:1)

Sources & evidence

ORD record
ord-62dc93b0143544daa1bb525ad9c76f7e
Source dataset
uspto-grants-2011_12
Patent number
US08084611B2

Reaction notes

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