Hydrochloric Acid → HCID 66917020, compound

HRID 2281602Notes

Reaction equation

HRID 2281602 reaction equation
C(=[N:14][CH:15]([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@@H:29]2[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30]2)=[CH:23][CH:22]=1)[C:16]#[N:17])(C1C=CC=CC=1)C1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>C1COCC1>[NH2:14][CH:15]([CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C@@H:29]2[CH2:33][O:32][C:31]([CH3:35])([CH3:34])[O:30]2)=[CH:23][CH:22]=1)[C:16]#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 866419092-(benzhydrylidene-amino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]pentanenitrile

Product 1

HCID 66917020HCID 66917020, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(benzhydrylidene-amino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]pentanenitrile (7.2 g, 15.5 mmol) in THF (50 ml) is added a 2M HCl (aq) (5 ml). The solution is heated at 40° C. for 4 hours and then allowed to cool to room temperature. The pH is adjusted to pH 9-10 using saturated aqueous sodium hydrogen carbonate solution and the organic solvent is removed in vacuo. The crude residue is dissolved in EtOAc (100 ml) and washed with water, brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified by chromatography on silica eluting with 5:1 to 1:1 iso-hexane/ethyl aEtOAc and 1% triethylamine to yield 2-Amino-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile as a colourless oil which solidifies; 1H NMR (CDCl3): mixture of diastereoisomers 1.39 (3H, s), 1.43 (3H, s), 1.70-1.87 (4H, m), 2.60 (2H, tr, J=7.1 Hz), 3.62 (1H, br), 3.90 (2H, m), 4.00-4.18 (2H, m), 4.48 (1H, pent, J=6.9 Hz), 6.82 (2H, d, J=7.4 Hz), 7.10 (2H, d, J=7.4 Hz). [M+H]+ 305

Workup

  1. temperatureto cool to room temperature
  2. customthe organic solvent is removed in vacuo
  3. dissolutionThe crude residue is dissolved in EtOAc (100 ml)
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue is purified by chromatography on silica eluting with 5:1 to 1:1 iso-hexane/ethyl aEtOAc and 1% triethylamine

Sources & evidence

ORD record
ord-dbd8c311a8ab4f18aa1e5279898c17d9
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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