(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)-16,18-difluoro-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
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)-16,18-difluoro-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]acetate | HCID 131736660 | — |
| Product | (2S)-2-(tert-Butoxy)-2-[(22S)-16,18-difluoro-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 131736661 | 53% |
Reaction Steps
Prepared in 53% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,18-difluoro-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]acetate 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 8.05 (d, J=7.7 Hz, 1H), 7.98 (s, 1H), 7.76 (s, 1H), 7.51 (t, J=7.7 Hz, 1H), 7.29 (s, 1H), 7.24 (d, J=7.3 Hz, 1H), 7.07 (d, J=11.0 Hz, 1H), 6.91 (t, J=8.4 Hz, 1H), 6.07-5.98 (m, 1H), 5.91 (br. s., 1H), 5.74 (d, J=15.4 Hz, 1H), 4.70 (d, J=5.9 Hz, 1H), 4.03 (t, J=11.2 Hz, 1H), 3.95 (br. s., 2H), 3.61 (t, J=11.0 Hz, 1H), 3.11 (br. s., 1H), 2.61 (d, J=8.8 Hz, 1H), 2.49-2.43 (m, 1H), 2.40 (s, 3H), 2.27-2.16 (m, 1H), 1.97-1.84 (m, 2H), 1.70 (d, J=7.3 Hz, 2H), 1.24 (s, 3H), 1.18 (s, 9H), 1.08 (d, J=5.9 Hz, 3H); LCMS (ESI, M): 659.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-9fe077f2a98b4b34a8e6e16223e143fa |
| Source note | uspto-grants-2016_08 |