Ethyl Acetate → HCID 131723494, compound
Reaction equation
[CH2:1]([NH:13][C:14](=[O:40])[C:15]1[CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[C:18](OCCO)=[C:17]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[F:39])[CH:16]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CO.CC[O:45][C:46]([CH3:48])=[O:47].CC[O:51]C(C)=O.[K+].[Br-]>C(O)=O>[CH2:1]([NH:13][C:14]([C:15]1[CH:16]=[C:17]([C:33]2[C:34]([F:39])([O:51][CH2:48][C:46]([OH:45])=[O:47])[CH2:35][CH:36]=[CH:37][CH:38]=2)[CH:18]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH:20]=1)=[O:40])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared as a white solid (0.229 g, 47%) from N-dodecyl-3-(2-fluorophenyl) 5-(4-methoxyphenyl)-4-(2-hydroxyethoxy)benzamide using a procedure similar to step 3 of example 1. The product was purifed by preparatory plate chromatography (4% Methanol/EtOAc) followed by flash chromatography (15% EtOAc/Hex and 20% EtOAC/Hex, both with 1% formic acid); 1H NMR (400 MHz, DMSO-d6) 80.84 (t, J=6.8 Hz, 3H), 1.17-1.27 (m, 18H), 1.44-1.51 (m, 2H), 3.22 (dd, J=6.8, 13.0 Hz, 2H), 3.78 (s, 3H), 3.81 (s, 2H), 6.99-7.02 (m, 2H), 7.23-7.28 (m, 2H), 7.42-7.47 (m, 2H), 7.50-7.57 (m, 2H), 7.71 (d, J=2.2 Hz, 1H), 7.84 (d, J=2.4 Hz, 1H), 8.47 (t, J=5.5, 1H), 12.48 (broad s, 1H); IR (KBr) 3375, 2925, 2850, 1730, 1615, 1200 cm−1; mass spectrum [(+)ESI], m/z 564 (M+H)+; Anal. Calcd. for C34H42FNO: C, 72.44; H, 7.51; N, 2.48, Found: C, 72.48; H, 7.67; N, 2.46.
Sources & evidence
- ORD record
- ord-b4b01a803d25449fac959efbbe19f98e
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06765021B2
Reaction notes
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