Hydrochloric Acid → HCID 86610698, compound

HRID 506406Notes

Reaction equation

HRID 506406 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[O:20][C:21]([CH2:29][C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=3)=[C:22]([C:24]([O:26]CC)=[O:25])[N:23]=2)[CH2:8][C@H:7]1[CH2:44][CH3:45])=[O:5])[CH3:2].O.[OH-].[Li+].Cl.C(OCC)(=O)C>CO.O>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[N:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=2)[C@@H:9]([NH:18][C:19]2[O:20][C:21]([CH2:29][C:30]3[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[C:32]([C:40]([F:41])([F:42])[F:43])[CH:31]=3)=[C:22]([C:24]([OH:26])=[O:25])[N:23]=2)[CH2:8][C@H:7]1[CH2:44][CH3:45])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 86610697HCID 86610697, compound

Product 1

HCID 86610698HCID 86610698, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-(4-ethoxycarbonyloxazol-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (200 mg) and lithium hydroxide monohydrate (78 mg) are dissolved in a mixture of methanol (3 ml) and water (500 μl), and the mixture is stirred at room temperature for 2 hours. The reaction solution is acidified by adding 2N aqueous HCl solution, then added ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)benzyl]-(4-carboxyoxazol-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (190 mg). MS (m/z): 617 [M+H]+.

Workup

  1. washThe organic layer is washed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7583a1c7fc804be7b2c8d9863354e3ff
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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