Acetaldehyde → HCID 59620346, compound

HRID 1887757Notes

Reaction equation

HRID 1887757 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:9](=[O:19])[CH:8]([NH:20][C:21](=[O:41])[C@H:22]([NH:27][C:28](=[O:40])[C:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:31])[CH3:30])[CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:7]2.[CH:42](=O)[CH3:43].C(#N)C.C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:42]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[C:9](=[O:19])[CH:8]([NH:20][C:21](=[O:41])[C@H:22]([NH:27][C:28](=[O:40])[C:29]([NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:30])[CH3:31])[CH2:23][CH:24]([CH3:25])[CH3:26])[CH2:7]2)[CH3:43]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 68411742HCID 68411742, compound

Product 1

HCID 59620346HCID 59620346, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

tert-Butyl 1-((2R)-1-(8-amino-2-oxo-1-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydroquinolin-3-ylamino)-4-methyl-1-oxopentan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (59 mg) and acetaldehyde (29 μL) were sequentially added to acetonitrile (730 μL), and sodium cyanoborohydride (7 mg) and acetic acid (18 μL) were added to the mixture under cooling on ice, followed by stirring for 5 minutes. The resultant mixture was extracted with ethyl acetate and saturated aqueous sodium bicarbonate solution, and the aqueous layer was further extracted with ethyl acetate. The organic layers were combined, and the combined organic layer was washed with saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. The solvent was evaporated under reduced pressure, and the thus-recovered residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1), whereby the title compound (58 mg) was yielded.

Workup

  1. additionwere added to the mixture
  2. temperatureunder cooling on ice
  3. extractionThe resultant mixture was extracted with ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. extractionthe aqueous layer was further extracted with ethyl acetate
  5. washthe combined organic layer was washed with saturated aqueous sodium chloride solution
  6. dry with materialby drying over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe thus-recovered residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:1), whereby the title compound (58 mg)
  9. customwas yielded

Sources & evidence

ORD record
ord-a99a27bb1e7d4eadaaad4fd09b4dbe03
Source dataset
uspto-grants-2013_08
Patent number
US08501772B2

Reaction notes

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