Acetone → HCID 86610630, compound

HRID 506386Notes

Reaction equation

HRID 506386 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]([CH2:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([C:36]([F:39])([F:38])[F:37])[CH:27]=3)[C:22]([NH:40][C:41]([O:43][CH2:44][CH2:45][OH:46])=[O:42])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2].CC(C)=[O:51]>S(=O)(=O)(O)O.[O-2].[Cr+6].[O-2].[O-2]>[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]([CH2:25][C:26]3[CH:27]=[C:28]([C:36]([F:37])([F:39])[F:38])[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=3)[C:22]([NH:40][C:41]([O:43][CH2:44][C:45]([OH:51])=[O:46])=[O:42])=[CH:21][N:20]=2)[CH2:8][C@H:7]1[CH2:47][CH3:48])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 180AcetoneHCID 86610631HCID 86610631, compound

Product 1

HCID 86610630HCID 86610630, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1118Sulfuric AcidSolvent

Procedure

(2R,4S)-4-{[3,5-Bis(trifluoromethyl)benzyl]-[5-(2-hydroxyethoxy-carbonylamino)pyrimidin-2-yl]}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (192 mg) is dissolved in acetone (5 ml), and thereto is added 2.67M chromium (VI) oxide in dilute sulfuric acid solution (320 μl) under ice-cooling. The mixture is stirred for 4.5 hours, and partitioned by adding sodium bisulfite, water and ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The resulting residue is purified by column chromatography (silica gel; chloroform:methanol=9:1→7:3) to give (2R,4S)-4-{[3,5-bis(trifluoromethyl)-benzyl]-(5-carboxymethoxycarbonylaminopyrimidin-2-yl)}amino-2-ethyl-6-methoxy-3,4-dihydro-2H-[1,5]naphthyridine-1-carboxylic acid ethyl ester (78 mg). MS (m/z): 701 [M+H]+.

Workup

  1. temperaturecooling
  2. custompartitioned
  3. additionby adding sodium bisulfite, water and ethyl acetate
  4. washThe organic layer is washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue is purified by column chromatography (silica gel; chloroform:methanol=9:1→7:3)

Sources & evidence

ORD record
ord-94365094d0a04e2883c18febcc22900c
Source dataset
uspto-grants-2010_08
Patent number
US07781443B2

Reaction notes

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