Methyl(2S)-2-(tert-butoxy)-2-[(22S)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-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)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-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)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-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 118319893 | — |
| 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)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-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 118319892 | 15% |
Reaction Steps
Prepared in 15.0% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-4,5,22,28-tetramethyl-17-(trifluoromethoxy)-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 8.19 (d, J=8.1 Hz, 1H), 8.13 (s, 1H), 8.01 (s, 1H), 7.55 (t, J=7.7 Hz, 1H), 7.37-7.30 (m, 3H), 7.29-7.24 (m, 1H), 6.01 (br. s., 1H), 4.70 (br. s., 1H), 3.85 (t, J=10.8 Hz, 1H), 3.64 (t, J=11.6 Hz, 1H), 3.46 (br. s., 2H), 3.10 (d, J=8.4 Hz, 1H), 2.63 (d, J=8.8 Hz, 1H), 2.51 (br. s., 3H), 2.31 (s, 3H), 1.93-1.51 (m, 10H), 1.19 (s, 3H), 1.16 (s, 9H), 1.12 (d, J=5.9 Hz, 3H); LCMS (ESI, M+1): 724.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-a77843bdb80e4be1be3773f2837cf4c5 |
| Source note | uspto-grants-2016_08 |