(2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane → HCID 86622337, compound

HRID 501705Notes

Reaction equation

[O:1]1[CH2:3][C@@H:2]1[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:20]([O:23][CH:24]1[CH2:32][C:31]2[C:26](=[CH:27][C:28]([O:33][CH3:34])=[CH:29][CH:30]=2)[CH:25]1[NH2:35])[CH:21]=[CH2:22]>C(#N)C>[CH2:20]([O:23][C@H:24]1[CH2:32][C:31]2[C:26](=[CH:27][C:28]([O:33][CH3:34])=[CH:29][CH:30]=2)[C@H:25]1[NH:35][CH2:3][C@@H:2]([OH:1])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:21]=[CH2:22]

Participants

Conditions

Temperature: 45 °C

Procedure

Step AE (4): A solution of tert-butyl (S)-1-((S)-oxiran-2-yl)-2-phenylethylcarbamate (298 mg) and LiClO4 (mg) in acetonitrile (3.0 mL) was stirred at rt for 10 min. To the above solution was added 1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-amine from Step AE (3) (137 mg) in acetonitrile (0.50 mL), and the reaction mixture was heated at 45° C. for 36 h. Solvents were removed in vacuo, and the residue was purified by HPLC to give tert-butyl (2S,3R)-4-((1R,2S)-2-(allyloxy)-6-methoxy-2,3-dihydro-1H-inden-1-ylamino)-3-hydroxy-1-phenylbutan-2-ylcarbamate as an oil (77 mg). retention time: 1.85 min (method B). MS (ESI) (M+H)+ 483.30.

Workup

customSolvents were removed in vacuo
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-b6d3daa3a3a24211ba08fcf10bf77452
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772221B2

Reaction notes

Loading…