Ethylene Glycol → HCID 15950258, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([C@@H:16]([NH:21][C:22](=[O:33])[O:23][C:24]2C=CC([N+]([O-])=O)=C[CH:25]=2)[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:10]=1.C(O)C[OH:42]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([C@@H:16]([NH:21][C:22](=[O:33])[O:23][CH2:24][CH2:25][OH:42])[C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C@H:11]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:10]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-nitrophenyl (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylcarbamate (36-1, 500 mg, 0.93 mmol, 1.0 equiv) and ethylene glycol (3 mL, excess) was heated at 100° C. for 1 h. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography on silica gel. Elution with 20% ethyl acetate/dichloromethane to 50% ethyl acetate/dichloromethane gave 2-hydroxyethyl (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylcarbamate (36-2) as a colorless foam. 1H NMR (500 MD, CDCl3) major rotamer: δ 7.38-7.21 (m, 5H), 7.11-6.94 (m, 3H), 6.40 (s, 1H), 5.92 (m, 1H), 5.51 (m, 1H), 5.07 (d, 1H, J=13 Hz), 4.91 (m, 1H), 4.37 (d, 1H, J=10 Hz), 4.20 (m, 2H), 3.81 (t, 2H, J=4.5 Hz), 3.64 (t, 1H, J=4 Hz),) 0.91 (s, 9H). LRMS m/z (M+H) 459.3 found, 459.2 required.