Triethylamine → HCID 136346652, compound

HRID 1971284Notes

Reaction equation

[O:1]=[C:2]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:3]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:4](=O)[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.CCN(CC)CC.Cl.[NH2:33][OH:34]>O1CCOCC1>[C:15]([O:14][C:13]([NH:12][CH:3]([C:4](=[N:33][OH:34])[C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)[C:2]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:1])=[O:19])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of tert-butyl (±)-1,3-dioxo-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-2-ylcarbamate TTA 08120 (0.20 g, 0.60 mmol) in 10 mL of dioxane were added Et3N (125 μl, 0.90 mmol) and hydroxylamine hydrochloride (65 mg, 0.90 mmol). The mixture was stirred 2 h at 110° C. in a sealed tube then dioxane was evaporated. The obtained residue was purified by column chromatography (SiO2, CH2Cl2:MeOH=9:1 to 97:3) to give (±)-2-tert-butyloxycarbonylamino-3-(hydroxyimino)-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one TTA 08160 (100 mg, 48% yield) as an oil.

Workup

customdioxane was evaporated
customThe obtained residue was purified by column chromatography (SiO2, CH2Cl2:MeOH=9:1 to 97:3)

Sources & evidence

ORD record: ord-52cd1921be434ec194c70a11fe027433
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431599B2

Reaction notes

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