(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-4'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5'-fluoro-4'-methyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate | HCID 118308875 | — |
| Reactant | ethyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate | HCID 131736663 | — |
| Product | Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate | HCID 123141276 | 82% |
Reaction Steps
Prepared in 82% yield from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(5′-fluoro-4′-methyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate following the procedure for ethyl(2S)-2-(tert-butoxy)-2-[(22S)-18-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18,24-undecaen-3-yl]acetate. 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=7.8 Hz, 1H), 8.08 (s, 1H), 8.04 (s, 1H), 7.54-7.49 (m, 1H), 7.32 (s, 1H), 7.29 (d, J=1.3 Hz, 1H), 7.03 (d, J=10.3 Hz, 1H), 6.83 (d, J=6.5 Hz, 1H), 6.25-6.14 (m, 1H), 6.05 (br. s., 1H), 5.86-5.75 (m, 1H), 4.51-4.40 (m, 1H), 4.10-3.93 (m, 3H), 3.78 (t, J=10.9 Hz, 1H), 3.69 (s, 3H), 3.07 (d, J=7.8 Hz, 1H), 2.69 (d, J=7.5 Hz, 1H), 2.51-2.47 (m, 1H), 2.46 (s, 3H), 2.41-2.35 (m, 1H), 2.32 (d, J=1.5 Hz, 3H), 1.98 (t, J=12.8 Hz, 2H), 1.82-1.70 (m, 2H), 1.33 (s, 3H), 1.25 (s, 9H), 1.06 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1): 670.25.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-ff8cfb0abfcf4e8895a9ae52fc338763 |
| Source note | uspto-grants-2016_08 |