Triethylamine → HCID 178438348, compound

HRID 1480125Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]([C:17]#[N:18])([CH3:16])[CH2:12][CH:13]1[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[NH2:28][OH:29]>C(O)C>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]([C:17](=[NH:18])[NH:28][OH:29])([CH3:16])[CH2:12][CH:13]1[CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (1-Cyano-2-cyclopropyl-1-methyl-ethyl)-carbamic acid benzyl ester (Example 66b, 795 mg, 3.08 mmol) in ethanol (10 ml) were added triethylamine (343 mg, 472 μl, 3.39 mmol) and hydroxylamine hydrochloride (214 mg, 3.08 mmol). The reaction mixture was stirred at 60° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (640 mg, 71%) as a white solid. MS (ESI, m/z): 292.5 (M+H+).

Workup

concentrationThe reaction mixture was concentrated in vacuo
dissolutionThe residue was dissolved in ethyl acetate
extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
dry with materialThe organic phase was dried over sodium sulfate
customevaporated down to dryness
customThe crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient

Sources & evidence

ORD record: ord-4ccad661abf5469396fc48c744ffe089
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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