HCID 60111230, compound → HCID 87904699, compound
Reaction equation
[CH3:1][O:2][O:3][P:4](OCCOC(N1C2C(=CC=CC=2)/C(=C/C2NC(C)=CC=2C)/C1=O)=O)([O:6][O:7][CH3:8])=[O:5].[OH:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)/[C:42](=[CH:49]/[C:50]2[NH:51][C:52]([CH3:56])=[CH:53][C:54]=2[CH3:55])/[C:41]1=[O:57])=[O:39]>>[CH3:1][O:2][O:3][P:4]([O:33][CH2:34][CH2:35][CH2:36][O:37][C:38]([N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)/[C:42](=[CH:49]/[C:50]2[NH:51][C:52]([CH3:56])=[CH:53][C:54]=2[CH3:55])/[C:41]1=[O:57])=[O:39])([O:6][O:7][CH3:8])=[O:5]Participants
Procedure
3-[1-(3,5-Dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 3-(dimethoxy-phosphonooxy)-propyl ester was prepared using the same protocol for synthesizing 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-(dimethoxy-phosphonooxy)-ethyl ester by replacing 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-hydroxy-ethyl ester with 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 3-hydroxy-propyl ester with a yield of (31%). 1H NMR (400 MHz, CDCl3) δ 12.63 (s, br, 1H, NH-1′), 7.82–7.84 (m, 1H, H-4), 7.48–7.52 (m, 1H, H-7), 7.41 (s, 1H, H-vinyl), 7.17–7.24 (m, 2H, H-5, 6), 6.04 (s, br, 1H, H-4′), 4.61 (t, J=6.25 Hz, 2H, NCOOCH2CH2CH2OPO(OCH3)2-1), 4.31 (q, J=6.38, 10.94 Hz, 2H, NCOOCH2CH2CH2OPO(OCH3)2-1), 3.80 (s, 3H, NCOOCH2CH2CH2OPO(OCH3)2-1), 3.77 (s, 3H, NCOOCH2CH2CH2OPO(OCH3)2-1), 2.40 (s, 3H, CH3), 2.35 (s, 3H, CH3), and 2.23–2.29 (m, 2H, NCOOCH2CH2CH2OPO(OCH3)2-1). 13P NMR (162 MHz, CDCl3) δ 2.40.
Sources & evidence
- ORD record
- ord-38652e9ba4bd46ecaae16124b41bd3a5
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07053114B2
Reaction notes
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