Potassium Bromide → HCID 23378960, compound

HRID 1279751Notes

Reaction equation

[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[Se:9])[N:5]1[C:10](=[O:25])[CH:11]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:12]([OH:16])[CH:13]=[CH:14][CH3:15])[CH3:3].[K+].[Br-]>>[CH3:1][CH:2]([C@H:4]1[CH2:8][O:7][C:6](=[Se:9])[N:5]1[C:10](=[O:25])[CH:11]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH:12]([OH:16])[CH2:13][CH2:14][CH3:15])[CH3:3]

Participants

Reactant 2

HCID 253877Potassium Bromide

HCID 86758506HCID 86758506, compound

Product 1

HCID 23378960HCID 23378960, compound

Procedure

(4S)-4-(1-methylethyl)-3-[3-hydroxyl-2-(phenylmethoxy)-1-oxo-4-hexen-1-yl]-2-oxazolidineselone, Yield: 85.0%. IR (KBr, cm−1) 3600, 3027.8, 2964.8, 2859.7, 1725.4, 1480.3, 1398.3, 1277.3, 1200.3, 1144.2, 1018.2, 829.1, 752.1, 703.1, 584.1; 1H NMR δ 7.40 (m, 4H), 6.63 (d, 1H, J=3.6 Hz), 5.80 (m, 2H), 4.71 (m, 4H), 4.40 (m, 2H), 2.58 (d, 1H, J=7.8 Hz), 2.27 (dhep, 1H, J=7.0 Hz, J=3.7 Hz), 1.75 (d, 3H, J=6.0 Hz), 0.94 (d, 3H, J=7.0 Hz), 0.88 (d, 3H, J=6.9 Hz); 13C NMR δ 188.92, 171.67, 136.98, 129.30, 128.72, 128.31, 128.16, 78.93, 73.88, 73.49, 69.81, 63.93, 28.65, 18.05, 17.82, 14.81; 77Se NMR δ 441.94 (d, J=4.9 Hz). HRMS (FAB) m/z 412.1039 (412.1028 calcd for C19H26NO4Se, M+H).

Sources & evidence

ORD record: ord-33bb2c003fb243989aa9876f8c72f8f9
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448409B1

Reaction notes

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