Citric Acid → HCID 86610576, compound

HRID 506346Notes

Reaction equation

HRID 506346 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[N:24]=[C:23](OC)[C:22](C(OCC)=O)=[C:21]([CH2:32][C:33]3[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=3)[N:20]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2].[OH-].[Na+].C(O)(=O)C[C:53](CC(O)=O)([C:55]([OH:57])=[O:56])[OH:54]>CO>[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[N:20]=[C:21]([CH2:32][C:33]3[CH:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=[C:35]([C:43]([F:45])([F:46])[F:44])[CH:34]=3)[C:22]([O:54][CH2:53][C:55]([OH:57])=[O:56])=[CH:23][N:24]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 86610577HCID 86610577, compound

Product 1

HCID 86610576HCID 86610576, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-(5-ethoxycarbonyl-methoxypyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (128 mg) is dissolved in methanol (3 ml), then thereto is added 1M aqueous sodium hydroxide solution (2 ml), and the mixture is stirred at room temperature for 2 hours. To the reaction mixture is added 10% aqueous citric acid solution, and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform:methanol=19:1) to give (2R*,4S*)-4-{[3,5-bis(trifluoromethyl)benzyl]-(5-carboxymethoxypyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (100 mg). MS (m/z): 658 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by column chromatography (silica gel; chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-fa8874d51f154e8bbcc7c83d0a880146
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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