methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate → tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-12,12-difluoro-2-hydroxy-2-(2-methoxy-ethyl)-nonadec-4-enoate
Reaction equation
[F:1][C:2]([F:35])([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[C@H:11]([C:25]([O-])=[O:26])[C@@:12]([OH:24])([CH2:20][CH2:21][O:22][CH3:23])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(C1(CCCCCC/C=C/[C@H](C([O-])=O)[C@@](O)(CCOC)C(OC(C)(C)C)=O)OCCO1)CCCCCC.[NH2:73][C@@H:74]([CH2:79][C:80]1[CH:85]=[CH:84][C:83]([O:86][CH2:87][CH2:88][CH2:89][CH3:90])=[CH:82][CH:81]=1)[C:75]([O:77][CH3:78])=[O:76]>>[CH2:87]([O:86][C:83]1[CH:82]=[CH:81][C:80]([CH2:79][C@H:74]([NH:73][C:25]([C@@H:11](/[CH:10]=[CH:9]/[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:1])([F:35])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C@@:12]([OH:24])([CH2:20][CH2:21][O:22][CH3:23])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:26])[C:75]([O:77][CH3:78])=[O:76])=[CH:85][CH:84]=1)[C:88]#[C:89][CH3:90]Participants
4
Reactant 3
Product 1
Procedure
No. 6804236 was obtained by the synthetic method in Step A-4 (dehydration condensation with 1-[bis(dimethylamino)methyliumyl]-1H-1,2,3-triazolo[4,5-B]pyridine-3-oxide hexafluorophosphate), except that No. 5553644, 1-tert-butyl (2S,3S)-3-((E)-9,9-difluoro-hexadec-1-enyl)-2-hydroxy-2-(2-methoxy-ethyl)-succinate was used instead of No. 6801710, 1-tert-butyl (2S,3S)-3-[(E)-8-(2-heptyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2-hydroxy-2-(2-methoxy-ethyl)-succinate, and methyl (S)-2-amino-3-(4-butoxy-phenyl)-propionate was used instead of methyl (S)-2-amino-3-(4-but-2-ynyloxy-phenyl)-propionate.
Sources & evidence
- ORD record
- ord-495370f13cf44a08a8350a1f67347ac5
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266853B2
Reaction notes
Loading…