Hydroxyamine hydrochloride → HCID 178436628, compound

HRID 245088Notes

Reaction equation

[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:16]([CH3:17])=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[CH2:18][CH3:19])[CH2:4][O:3]1.C([O-])(O)=O.[Na+].Cl.[NH2:27][OH:28]>CO>[CH3:1][C:2]1([CH3:20])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:16]([CH3:17])=[CH:15][C:12]([C:13]([NH:27][OH:28])=[NH:14])=[CH:11][C:10]=2[CH2:18][CH3:19])[CH2:4][O:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a mixture of (R)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-3-ethyl-5-methyl-benzonitrile (4.45 g, 16.2 mmol) and NaHCO3 (4.75 g, 56.6 mmol) in methanol (30 mL), hydroxylamine hydrochloride (3.37 g, 48.5 mmol) is added. The mixture is stirred at 60° C. for 18 h before it is filtered and the solvent of the filtrate is removed in vacuo. The residue is dissolved in EA and washed with a small amount of water and brine. The org. phase is separated, dried over MgSO4, filtered, concentrated and dried to give the title compound (5.38 g) as a white solid; LC-MS**: tR=0.46 min, [M+1]+=309.23; 1H NMR (D6-DMSO): δ 1.17 (t, J=7.5 Hz, 3H), 1.33 (s, 3H), 1.38 (s, 3H), 2.25 (s, 3H), 2.57-2.69 (m, 2H), 3.73-3.84 (m, 3H), 4.12 (t, J=7.0 Hz, 1H), 4.39-4.45 (m, 1H), 5.76 (s br, 2H), 7.34 (s, 1H), 7.36 (s, 1H), 9.47 (s, 1H).

Workup

additionis added
filtrationis filtered
customthe solvent of the filtrate is removed in vacuo
dissolutionThe residue is dissolved in EA
washwashed with a small amount of water and brine
customphase is separated
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customdried

Sources & evidence

ORD record: ord-787fe59449ef4637bc61e4fcfd0aeef5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658675B2

Reaction notes

Loading…