(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 → (2S)-2-(tert-Butoxy)-2-[(22S)-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),16,18,24-undecaen-3-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| 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 | — |
| Reactant | Methyl(2S)-2-(tert-butoxy)-2-[(22S)-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),16,18,24-undecaen-3-yl]acetate | HCID 123687506 | — |
| Product | (2S)-2-(tert-Butoxy)-2-[(22S)-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),16,18,24-undecaen-3-yl]acetic acid | HCID 123559938 | 60% |
Reaction Steps
Prepared from methyl(2S)-2-(tert-butoxy)-2-[(22S)-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),16,18,24-undecaen-3-yl]acetate in 60% yield following the same procedure as (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 (500 MHz, DMSO-d6) δ 8.06 (d, J=8.5 Hz, 1H), 8.04 (s, 1H), 8.00 (s, 1H), 7.52 (t, J=7.5 Hz, 1H), 7.36-7.28 (m, 2H), 7.18-7.13 (m, 2H), 7.12-7.07 (m, 1H), 6.17-6.06 (m, 1H), 5.92 (br. s., 1H), 5.77 (d, J=15.9 Hz, 1H), 4.57 (br. s., 1H), 4.05-3.90 (m, 3H), 3.64 (t, J=11.0 Hz, 1H), 3.13 (br. s., 1H), 2.64 (d, J=10.7 Hz, 1H), 2.58-2.53 (m, 1H), 2.41 (s, 3H), 2.30 (s, 3H), 2.28-2.20 (m, 1H), 1.96 (d, J=13.1 Hz, 1H), 1.88 (d, J=13.4 Hz, 1H), 1.72 (br. s., 2H), 1.26 (s, 3H), 1.19 (s, 9H), 1.02 (d, J=5.8 Hz, 3H); LCMS (ESI, M+1): 638.5.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-8089aaabc9644cd699cbf031875c5ed8 |
| Source note | uspto-grants-2016_08 |