Methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-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-decaen-3-yl]acetate → (2S)-2-(tert-Butoxy)-2-[(22S)-8-chloro-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-decaen-3-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-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-decaen-3-yl]acetate | HCID 118316300 | — |
| Reactant | (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]acetic acid | HCID 123621546 | — |
| Product | (2S)-2-(tert-Butoxy)-2-[(22S)-8-chloro-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-decaen-3-yl]acetic acid | HCID 118316301 | 97% |
Reaction Steps
Prepared in 97% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-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-decaen-3-yl]acetate following the procedure for (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]acetic acid. 1H NMR (600 MHz, DMSO-d6) δ 8.31 (s, 1H), 7.83 (d, J=7.7 Hz, 1H), 7.55 (t, J=7.7 Hz, 1H), 7.41 (d, J=7.3 Hz, 1H), 7.30 (br. s., 1H), 7.14 (d, J=6.2 Hz, 1H), 7.10 (d, J=10.3 Hz, 1H), 5.86-5.58 (m, 1H), 4.60 (d, J=4.4 Hz, 1H), 4.00-3.95 (m, 1H), 3.90 (br. s., 1H), 3.84-3.77 (m, 1H), 3.47-3.41 (m, 1H), 3.38-3.32 (m, 1H), 2.43 (br. s., 3H), 2.34 (br. s., 1H), 2.28 (s, 3H), 2.01-1.49 (m, 10H), 1.19 (br. s., 3H), 1.16 (s, 9H), 1.03 (d, J=5.5 Hz, 3H); LCMS (ESI, M): 691.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-38833a7a5d7248bd9fa33501e87ca960 |
| Source note | uspto-grants-2016_08 |