Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-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)-16,17-difluoro-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)-16,17-difluoro-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 118316360 | — |
| 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)-16,17-difluoro-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 118316361 | 80% |
Reaction Steps
Prepared in 80.0% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-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 8.12 (d, J=7.8 Hz, 1H), 7.94 (s, 1H), 7.89 (s, 1H), 7.52 (t, J=7.7 Hz, 1H), 7.39 (q, J=9.6 Hz, 1H), 7.30 (d, J=7.5 Hz, 1H), 7.01 (d, J=7.0 Hz, 1H), 5.51 (s, 1H), 5.03 (br. s., 1H), 4.98 (d, J=11.3 Hz, 1H), 4.83 (d, J=11.3 Hz, 1H), 4.65 (br. s., 1H), 3.93-3.83 (m, 1H), 3.76 (br. s., 1H), 3.52-3.43 (m, 3H), 2.40 (s, 3H), 1.92 (d, J=12.0 Hz, 1H), 1.82-1.51 (m, 9H), 1.19 (s, 3H), 1.12 (s, 9H), 1.09 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1): 692.20.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-d0f44b3b3e254aff8110e58f535e46c5 |
| Source note | uspto-grants-2016_08 |