Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-chloro-17-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-decaen-3-yl]acetate → (2S)-2-(tert-Butoxy)-2-[(22S)-5-chloro-17-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-decaen-3-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-chloro-17-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-decaen-3-yl]acetate | HCID 118316379 | — |
| 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)-5-chloro-17-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-decaen-3-yl]acetic acid | HCID 118316377 | 19.1% |
Reaction Steps
Prepared in 19.1% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-chloro-17-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-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 8.31 (s, 1H), 7.84 (d, J=7.7 Hz, 1H), 7.57 (t, J=7.9 Hz, 1H), 7.44 (d, J=7.7 Hz, 1H), 7.33 (s, 1H), 7.27-7.21 (m, 1H), 7.17 (d, J=8.8 Hz, 2H), 5.75 (br. s., 1H), 4.60 (d, J=4.4 Hz, 1H), 4.01-3.86 (m, 2H), 3.50 (br. s., 1H), 3.37 (br. s., 4H), 2.42 (s, 3H), 2.33 (br. s., 1H), 1.96 (d, J=13.2 Hz, 1H), 1.88-1.73 (m, 3H), 1.70-1.47 (m, 6H), 1.18 (s, 3H), 1.16 (s, 9H), 1.02 (d, J=5.9 Hz, 3H); LCMS (ESI, M+1): 678.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-c7639a7e91db4a929a95713aafd8f241 |
| Source note | uspto-grants-2016_08 |