Allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate → Allyl trans-2-[3-(7-Bromo-6-ethylthioquinazolin-4(3H)-on-3-yl)-2-oxopropyl]-3-methoxy-1-piperidinecarboxylate
Reaction equation
C(O)=O.[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[S:16][CH2:17][CH3:18].Br[CH2:20][C:21](=[O:37])[CH2:22][C@H:23]1[C@H:28]([O:29][CH3:30])[CH2:27][CH2:26][CH2:25][N:24]1[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32]>>[Br:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=[O:15])[N:10]([CH2:20][C:21](=[O:37])[CH2:22][C@H:23]3[C@H:28]([O:29][CH3:30])[CH2:27][CH2:26][CH2:25][N:24]3[C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[CH:11]=[N:12]2)=[CH:7][C:6]=1[S:16][CH2:17][CH3:18]Participants
Procedure
In the manner of Example 4, 0.743 g (0.00224 mol) of 7-bromo-6-ethylthioquinazolin-4(3H)-one formic acid salt and 0.750 g (0.00224 mol) of allyl trans-2-(3-bromo-2-oxopropyl)-3-methoxy-1-piperidinecarboxylate were converted into the title compound. After flash chromatography on silica gel (eluant 3% methanol in chloroform) there was obtained the pure product: yield 0.61 g (51%) mass spectrum m/e 537 (molecular ion with expected isotope pattern), 41 (parent peak, CH2 =CH--CH2 +) among others. 1H--NMR(CDCl3) 1.4 ppm (triplet, 3H, SCH2CH3), 1.4-2.1 (multiplet, 4H, OCHCH2CH2CH2N), 2.8-3.4 (multiplet, 6H, NCH2, SCH2CH3, COCH2CH), 3.4 (singlet, 3H, OCH3), 4.0 (broad singlet, 1H, CHNCO), 4.6 (doublet, 2H, CH2CH=CH2), 5.0 (singlet, 2H, NCH2CO), 5.0-5.5 (multiplet, 2H, CH=CH2), 5.6-6.1 (octet, 1H, CH2 =CH), 7.3 (singlet, 1H, aromatic H), 7.9 (singlet, 2H, aromatic H, N=CH--N).
Sources & evidence
- ORD record
- ord-2df0f01e3aa8475f95a3c46159797973
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04920224
Reaction notes
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