methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 118316326 | — |
| Reactant | (2S)-2-(tert-Butoxy)-2-[(22S)-8-chloro-4,17,22,28-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 118332041 | — |
| Product | (2S)-2-(tert-Butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 118316327 | 27.2% |
Reaction Steps
Prepared in 27.2% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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)-8-chloro-4,17,22,28-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. 1H NMR (500 MHz, DMSO-d6) δ 8.70 (d, J=5.5 Hz, 2H), 8.13 (s, 1H), 8.05 (s, 1H), 7.87 (d, J=7.7 Hz, 1H), 7.45 (d, J=5.5 Hz, 3H), 7.31 (d, J=7.7 Hz, 1H), 7.22-7.12 (m, 3H), 5.91 (br. s., 1H), 4.60 (br. s., 1H), 3.92-3.81 (m, 1H), 3.62 (d, J=12.1 Hz, 1H), 3.44 (br. s., 4H), 2.19 (s, 3H), 1.93-1.65 (m, 9H), 1.54 (br. s., 1H), 1.20 (s, 3H), 1.18 (s, 9H), 1.06 (d, J=6.2 Hz, 3H). LCMS (ESI, M): 720.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-2636aa633abd4b97a1e93f8f20db14ca |
| Source note | uspto-grants-2016_08 |