Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(hydroxymethyl)-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-decaen-3-yl]acetate → (2S)-2-(tert-Butoxy)-2-[(22S)-17-fluoro-5-(hydroxymethyl)-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-decaen-3-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(hydroxymethyl)-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-decaen-3-yl]acetate | HCID 118316357 | — |
| 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-5-(hydroxymethyl)-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-decaen-3-yl]acetic acid | HCID 118316359 | 72.1% |
Reaction Steps
Prepared in 72.1% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(hydroxymethyl)-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-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 (400 MHz, DMSO-d6) δ 8.16 (s, 1H), 8.13 (d, J=7.8 Hz, 1H), 7.97 (s, 1H), 7.52 (t, J=7.7 Hz, 1H), 7.33 (d, J=7.8 Hz, 1H), 7.22 (dd, J=9.4, 2.6 Hz, 1H), 7.19-7.13 (m, 2H), 5.58 (br. s., 1H), 5.03 (br. s., 1H), 5.00-4.93 (m, 1H), 4.90-4.82 (m, 1H), 4.63 (br. s., 1H), 3.91-3.75 (m, 2H), 3.57-3.43 (m, 3H), 2.63 (d, J=10.0 Hz, 1H), 2.42 (s, 3H), 1.96-1.52 (m, 10H), 1.20 (s, 3H), 1.13 (s, 9H), 1.09 (d, J=5.8 Hz, 3H); LCMS (ESI, M+1): 674.6.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-ec22615608c94ec297dcf6e21f38e6e7 |
| Source note | uspto-grants-2016_08 |