Hydrochloric Acid → HCID 9945666, compound

HRID 901828Notes

Reaction equation

HRID 901828 reaction equation
[CH2:1]([O:3][CH:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[N:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:12][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2].Cl.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH2:1]([O:3][CH:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:14][CH:15]=1)[C:5]([O:7][CH3:8])=[O:6])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 67190078HCID 67190078, compound

Product 1

HCID 9945666HCID 9945666, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude methyl 2-ethoxy-3-[4-(N-heptylimiomethyl)phenyl]propanoate obtained in step (i) above (2.95 g), was dissolved in methanol (40 ml), and treated with conc. HCl (850 μl, 1 eq, 8.51 mmol) and sodium cyanoborohydride (535 mg, 1 eq, 8.51 mmol) at 0° C. The progress of the reaction was monitored by TLC. After 2-3 h, the reaction mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. The residue was chromatographed using methanol and chloroform to afford the title compound (1.71 g, yield 60%) as viscous liquid.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe residue was chromatographed

Sources & evidence

ORD record
ord-22d7f0c479cd400a83f423d02cde5f3e
Source dataset
uspto-grants-2008_04
Patent number
US07365064B2

Reaction notes

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