Sodium Iodide → HCID 68185410, compound

HRID 2366899Notes

Reaction equation

HRID 2366899 reaction equation
[CH3:1][CH:2]([O:4][C:5](=[O:22])[NH:6][C@H:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[N:10]([C:18](=[O:20])[CH3:19])[C@@H:9]([CH3:21])[CH2:8]1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:30][C:31](=[O:33])[CH3:32].[I-].[Na+]>CC(C)=O>[C:18]([N:10]1[C:11]2[C:16](=[CH:15][C:14]([NH:17][CH2:30][C:31](=[O:33])[CH3:32])=[CH:13][CH:12]=2)[C@H:7]([NH:6][C:5](=[O:22])[O:4][CH:2]([CH3:1])[CH3:3])[CH2:8][C@@H:9]1[CH3:21])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 68185409HCID 68185409, compound

Product 1

HCID 68185410HCID 68185410, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-methylethyl[(2S,4R)-1-acetyl-6-amino-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl]carbamate (for a preparation see Intermediate 112) (1.46 g, 4.78 mmol) in acetone (15 mL) at 60° C. was added potassium carbonate (0.991 g, 7.17 mmol) and the resulting mixture was stirred at this temperature for 15 min. 1-Chloro-2-propanone (0.457 ml, 5.74 mmol) was added as well as sodium iodide (0.860 g, 5.74 mmol) and resulting mixture was stirred at 60° C. for 1 h then cooled to room temperature, filtered through celite and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in Hexanes) gave 1-methylethyl {(2S,4R)-1-acetyl-2-methyl-6-[(2-oxopropyl)amino]-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (1.11 g, 3.07 mmol, 64%) as an orange foamy solid.

Workup

  1. customat 60° C.
  2. customresulting mixture
  3. stirringwas stirred at 60° C. for 1 h
  4. filtrationfiltered through celite and
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography on silica gel (gradient: 10 to 100% AcOEt in Hexanes)

Sources & evidence

ORD record
ord-a4ce7592025841719daf458bfdf2504c
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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