Water → HCID 178487614, compound

HRID 2202330Notes

Reaction equation

HRID 2202330 reaction equation
[N+](=[CH:3][Si](C)(C)C)=[N-].[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@@H:23]2[N:32]([C:33]([C@@H:35]3[CH2:38][C@H:37]([C:39]([OH:41])=[O:40])[CH2:36]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:42][CH3:43])[CH:26]=[CH:25][C:24]2=3)=[O:22])[CH:12]=[C:13]2[C:17]=1[C:16]([CH3:19])([CH3:18])[CH2:15][CH2:14]2.O.C(OCC)(=O)C>C1COCC1.CO>[F:8][C:9]1[CH:10]=[C:11]([NH:20][C:21]([C@@H:23]2[N:32]([C:33]([C@@H:35]3[CH2:38][C@H:37]([C:39]([O:41][CH3:3])=[O:40])[CH2:36]3)=[O:34])[CH2:31][CH2:30][C:29]3[N:28]=[C:27]([O:42][CH3:43])[CH:26]=[CH:25][C:24]2=3)=[O:22])[CH:12]=[C:13]2[C:17]=1[C:16]([CH3:18])([CH3:19])[CH2:15][CH2:14]2

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 167693TrimethylsilyldiazomethaneHCID 178487610HCID 178487610, compound

Product 1

HCID 178487614HCID 178487614, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Diazomethyl)trimethylsilane (0.6M hexane solution) (0.404 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 (60 mg, 0.12 mmol) in THF (1 mL) and MeOH (1 mL) at 5° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added water and ethyl acetate, the organic layer was separated, and the aqueous layer 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; 5→50% ethyl acetate/hexane) to give the title compound (50 mg, 0.098 mmol, 81%) as a colorless oil.

Workup

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

Sources & evidence

ORD record
ord-756a515a263d4557bbf6ce333e841d3b
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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