tert-Butyl cyanoacetate → Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate

HRID 2115707Notes

Reaction equation

HRID 2115707 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=O)[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18]([O:22][C:23]([NH:25][C@H:26]([CH:34]=O)[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:24])([CH3:21])([CH3:20])[CH3:19].[C:36]([CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])#[N:37].C([O-])(=O)C.[NH4+:50]>COCCOC>[NH2:37][C:36]1[NH:50][C:15]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:16][CH:34]([CH:26]([NH:25][C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:38]=1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]

Participants

6

Reactant 4

HCID 70693tert-Butyl cyanoacetateHCID 517165Ammonium AcetateHCID 5205131-[2-(Benzyloxy)phenyl]ethan-1-oneHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Product 1

HCID 22258838Tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylateYield 16.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of the starting compound 1A (3.000 g, 13.258 mmol), N-tert-butoxycarbonyl-phenylalaninal (3.305 g, 13.258 mmol), tert-butyl cyanoacetate (1.872 g, 13.258 mmol), ammonium acetate (3.066 g, 39.774 mmol) and 1,2-dimethoxyethane (5.0 mL) was heated at reflux for 6 hrs. After cooled to room temperature, the mixture was extracted with ethyl acetate and saturated NaHCO3 solution. The separated organic phase was washed with water and brine successively, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was triturated with diisopropyl ether to give tert-butyl 2-amino-6-[2-(benzyloxy)phenyl]4-{1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}-1,4-dihydro-3-pyridinecarboxylate as a yellow solid (1.281 g, yield; 16%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hrs
  3. extractionthe mixture was extracted with ethyl acetate and saturated NaHCO3 solution
  4. washThe separated organic phase was washed with water and brine successively
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-cccabbb7c75c4fb6b3e39d7b9fa0a1f5
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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