Water → HCID 178487616, compound

HRID 2202328Notes

Reaction equation

HRID 2202328 reaction equation
Cl[CH2:2][CH:3]1[CH:7]([CH3:8])[O:6][C:5](=[O:9])[O:4]1.[F:10][C:11]1[CH:12]=[C:13]([NH:22][C:23]([C@@H:25]2[N:34]([C:35]([C@@H:37]3[CH2:40][C@H:39]([C:41]([OH:43])=[O:42])[CH2:38]3)=[O:36])[CH2:33][CH2:32][C:31]3[N:30]=[C:29]([O:44][CH3:45])[CH:28]=[CH:27][C:26]2=3)=[O:24])[CH:14]=[C:15]2[C:19]=1[C:18]([CH3:21])([CH3:20])[CH2:17][CH2:16]2.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[F:10][C:11]1[CH:12]=[C:13]([NH:22][C:23]([C@@H:25]2[N:34]([C:35]([C@@H:37]3[CH2:40][C@H:39]([C:41]([O:43][CH2:2][C:3]4[O:4][C:5](=[O:9])[O:6][C:7]=4[CH3:8])=[O:42])[CH2:38]3)=[O:36])[CH2:33][CH2:32][C:31]3[N:30]=[C:29]([O:44][CH3:45])[CH:28]=[CH:27][C:26]2=3)=[O:24])[CH:14]=[C:15]2[C:19]=1[C:18]([CH3:20])([CH3:21])[CH2:17][CH2:16]2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135579654-Chloromethyl-5-methyl-1,3-dioxolan-2-oneHCID 178487610HCID 178487610, compound

Product 1

HCID 178487616HCID 178487616, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloromethyl-5-methyl-1,3-dioxolan-2-one (0.026 mL, 0.24 mmol) was added to a mixture of cis-3-(((5R)-5-((7-fluoro-1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)carbamoyl)-2-methoxy-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)carbonyl)cyclobutanecarboxylic acid (100 mg, 0.20 mmol) and potassium carbonate (33.5 mg, 0.24 mmol) in DMF (2.0 mL) at room temperature, and the mixture was stirred at room temperature for 5 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 20→50% ethyl acetate/hexane) to give the title compound (58.2 mg, 0.096 mmol, 47.5%) as a white amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 20→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-46ae7813d4bd473aa418f9dcf8b4ecd9
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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