tert-butyl N-[(1S)-2-phenyl-1-(prop-2-yn-1-ylcarbamoyl)ethyl]carbamate → (S)-tert-Butyl (1-(5-methyloxazol-2-yl)-2-phenylethyl)carbamate

HRID 339279Notes

Reaction equation

[O:1]=[C:2]([NH:19][CH2:20][C:21]#[CH:22])[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CC#N.[Au](Cl)(Cl)Cl>[CH3:22][C:21]1[O:1][C:2]([C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate (95 mg, 0.31 mmol) in MeCN (1.6 mL) was added gold (III) chloride (9.5 mg, 0.031 mmol). The resulting reaction mixture was stirred at 50° C. overnight and then purified directly using flash chromatography (gradient from 0% to 100% EtOAc/hexanes) to give the title compound (69 mg, 73%) as a colorless oil. %). 1H NMR (CDCl3) δ 7.37-7.17 (m, 3H), 7.05 (d, J=6.4 Hz, 2H), 6.63 (s, 1H), 5.12 (br s, 2H), 3.33-3.01 (m, 2H), 2.27 (d, J=1.1 Hz, 3H), 1.49-1.34 (m, 9H); MS (ESI+) m/z 303.3 (M+H)+.

Workup

customThe resulting reaction mixture
custompurified directly

Sources & evidence

ORD record: ord-6af741f6d4634b5f87a34302c5234ffc
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889712B2

Reaction notes

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