HCID 58109196, compound → HCID 58109491, compound

HRID 2037425Notes

Reaction equation

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

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 3-((S)-1-(3-methoxyphenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one Isomer 1 (0.1240 g, 0.381 mmol) and EtSNa (0.2115 g, 2.51 mmol) in DMF (2 mL) was heated at 170° C. for 2.5 h under nitrogen. The mixture was diluted with EtOAc, washed with 1 N aq HCl. The aqueous phase was extracted with EtOAc (2×). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford of 3-((S)-1-(3-hydroxyphenyl)ethyl)-6-methyl-6-phenyl-1,3-oxazinan-2-one (0.1036 g, 87%). LC-MS Method 1 tR=1.49 min, m/z 312 (MH+); 1H NMR (400 MHz, CDCl3) δ 7.59-7.53 (m, 1H), 7.40-7.28 (m, 5H), 7.19-7.15 (m, 1H), 6.98 (m, 1H), 6.83-6.75 (m, 2H), 5.74 (q, J=7.1 Hz, 1H), 2.80-2.67 (m, 2H), 2.30-2.25 (m, 1H), 2.09-2.01 (m, 1H), 1.62 (s, 3H), 1.25 (d, J=7.0 Hz, 3H).

Workup

washwashed with 1 N aq HCl
extractionThe aqueous phase was extracted with EtOAc (2×)
dry with materialThe combined organic phase was dried over Na2SO4
customAfter the solvents were evaporated
customthe residue was purified by chromatography on silica gel
washeluted with hexanes/EtOAc

Sources & evidence

ORD record: ord-3a4ea1c3bfa348fba285d1d6b354cb8a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

Loading…