Ethyl N-methylaminoacetate hydrochloride → HCID 57871423, compound
Reaction equation
[CH2:1]([C:3]([C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([C:33](O)=[O:34])[CH:27]=[CH:26]2)([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([CH2:20][CH3:21])[CH:14]([OH:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[C:8]([CH3:22])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].Cl.[CH2:37]([O:39][C:40](=[O:44])[CH2:41][NH:42][CH3:43])[CH3:38]>>[CH2:37]([O:39][C:40](=[O:44])[CH2:41][N:42]([C:33]([C:28]1[CH:27]=[CH:26][C:25]2[C:30](=[CH:31][CH:32]=[C:23]([C:3]([CH2:1][CH3:2])([C:6]3[CH:11]=[CH:10][C:9]([O:12][CH:13]([CH2:20][CH3:21])[CH:14]([OH:19])[C:15]([CH3:16])([CH3:17])[CH3:18])=[C:8]([CH3:22])[CH:7]=3)[CH2:4][CH3:5])[CH:24]=2)[CH:29]=1)=[O:34])[CH3:43])[CH3:38]Participants
Procedure
Following a procedure analogous to Example 7E esterify the diastereomeric isomer pair 1 of 6-{1-ethyl-1-[4-(1-ethyl-2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-naphthalene-2-carboxylic acid using N-methyl glycine ethyl ester hydrochloride to provide the title compound as a white foam (315 mg, 88%). 1NMR (400 MHz, CDCl3) δ ppm: 0.64 (t, J=7.2 Hz, 6H), 0.93 (t, J=8.4 Hz, 3H), 0.93 (s, 9H), 1.31 (m, 3H), 1.68 (m, 1H), 1.80 (m, 1H), 2.12 (s, 3H), 2.17 (q, 4H), 2.60 (bs, 1H), 3.11 (s, 2H), 3.16 (s, 1H), 3.27 (s, 1H), 4.05 (s, 0.73H), 4.27 (m, 3H), 4.32 (s, 1.27H), 6.63 (d, J=8.8 Hz, 1H), 6.90 (s, 1H), 6.93 (d, J=8.8 Hz, 1H), 7.16 (d, J=10.0 Hz, 1H), 7.49 (m, 1H), 7.55 (d, J=7.6 Hz, 1H), 7.68 (m, 1H), 7.81 (s, 1H), 7.87 (m, 2H). High Res. ES-MS: 598.3488; calc. for C36H49NO5+Na: 598.3509. Analysis for C36H49NO5; Calcd: C, 75.10; H, 8.58; N, 2.43. Found: C, 75.04; H, 8.58; N, 2.43.
Sources & evidence
- ORD record
- ord-6c03f8f7e4ac47748412e4ffeb9dbc52
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943795B2
Reaction notes
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