Triethylamine → (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate

HRID 449480

Reaction equation

ClC(Cl)(Cl)C(OC(=O)C(Cl)(Cl)Cl)=O.[NH2:14][C:15](=O)[C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)Cl>[C:15]([C@@H:16]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:34])[CH3:33])[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=1)#[N:14]

Participants

Conditions

Temperature: 0 °C

Procedure

Trichloroacetic acid anhydride (120 mg, 0.39 mmol) was added slowly to a solution of (S)-tert-butyl 1-amino-3-(4-isopropoxyphenyl)-1-oxopropan-2-ylcarbamate (50 mg, 0.2 mmol) in methylene chloride (3 mL) and triethylamine (86 uL, 0.62 mmol) at 0° C. The reaction was stirred for 1 h. at 0° C. The reaction was quenched with saturated NaHCO3 and was extracted with ethyl acetate. The organic phase was washed with water, saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product, which was purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1) to obtain the (S)-tert-butyl 1-cyano-2-(4-isopropoxyphenyl)ethylcarbamate (40 mg, 80%) as clear oil. Analytical LCMS (M+Na)+: m/z=327.0.

Workup

customThe reaction was quenched with saturated NaHCO3
extractionwas extracted with ethyl acetate
washThe organic phase was washed with water, saturated brine
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto give the crude product, which
customwas purified by Flash chromatography on a silica gel column (EtOAc:Hexane, 1:3 to 1:1)

Sources & evidence

ORD record: ord-ded7723687b84368be83e778da5e538d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481732B2

Linked notes

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