1,1'-Carbonyldiimidazole → HCID 118324853, compound

HRID 587866Notes

Reaction equation

HRID 587866 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C@@H:4]([CH2:12][CH2:13][C:14]([OH:16])=O)[CH2:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[F:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C@H:40]([NH2:42])[CH3:41])=[CH:32][CH:31]=1>CN(C=O)C>[F:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]([C@H:40]([NH:42][C:14](=[O:16])[CH2:13][CH2:12][C@@H:4]2[CH2:3][C:2](=[O:1])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5]2)[CH3:41])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 55278857HCID 55278857, compoundHCID 90003241HCID 90003241, compound

Product 1

HCID 118324853HCID 118324853, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of (R)-3-(4-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)propanoic acid (0.8 g, 3.67 mmol) (Crude) in dry DMF (15 mL), CDI (0.713 g, 4.40 mmol) was added. The reaction mixture was stirred at RT for 0.5 h. Then (R)-1-(4-fluoronaphthalen-1-yl)ethanamine (0.832 g, 4.40 mmol) was added and the reaction mixture was stirred at RT for 2 h. After completion of reaction ice was added to reaction mixture, solid precipitated out was filtered through Buchner funnel to get title compound (830 mg, 58.1%); m/z 390.54. Crude was taken without purification for next reaction.

Workup

  1. stirringthe reaction mixture was stirred at RT for 2 h
  2. customAfter completion of reaction ice
  3. additionwas added to reaction mixture, solid
  4. customprecipitated out
  5. filtrationwas filtered through Buchner funnel

Sources & evidence

ORD record
ord-43e1d5065e734c9db8a22f4984e91259
Source dataset
uspto-grants-2016_01
Patent number
US09227919B2

Reaction notes

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