Hydrochloric Acid → HCID 66917020, compound

HRID 1183037Notes

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

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 aqueous HCl (5 mL of a 2 M solution). The solution is heated at 40° C. for 4 h and then allowed to cool to RT. The pH is adjusted to 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 then dried (MgSO4), filtered and concentrated in vacuo. The resulting residue is purified by chromatography (SiO2, iso-hexane:EtOAc with 1% triethylamine) to yield the title compound as colourless oil that solidifies upon standing as a mixture of diastereoisomers. [M+H]+ 305.

Workup

temperatureto cool to RT
customthe organic solvent is removed in vacuo
dissolutionThe crude residue is dissolved in EtOAc (100 mL)
washwashed with water, brine
dry with materialthen dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue is purified by chromatography (SiO2, iso-hexane:EtOAc with 1% triethylamine)

Sources & evidence

ORD record: ord-6ee530804ca647d9938c19fc63f97427
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664228B2

Reaction notes

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