(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-decaen-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-decaen-3-yl]acetic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (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-decaen-3-yl]acetic acid | HCID 118316274 | — |
| 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-decaen-3-yl]acetate | HCID 118319914 | — |
| 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-decaen-3-yl]acetic acid | HCID 118319907 | 49% |
Reaction Steps
Prepared in 49% 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-decaen-3-yl]acetate following the same procedure as (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-decaen-3-yl]acetic acid. 1H NMR (500 MHz, DMSO-d6) δ 8.06 (d, J=7.7 Hz, 1H), 7.97 (s, 1H), 7.85 (s, 1H), 7.50 (t, J=7.7 Hz, 1H), 7.25 (s, 2H), 7.01 (d, J=11.4 Hz, 1H), 6.89 (t, J=9.5 Hz, 1H), 5.81 (br. s., 1H), 4.69 (t, J=5.3 Hz, 1H), 3.93-3.82 (m, 1H), 3.59 (t, J=11.2 Hz, 1H), 3.49-3.40 (m, 1H), 3.26 (d, J=7.0 Hz, 1H), 2.63 (d, J=9.9 Hz, 1H), 2.40 (s, 3H), 1.89-1.57 (m, 10H), 1.50 (d, J=7.7 Hz, 1H), 1.19 (s, 3H), 1.16 (s, 9H), 1.11 (d, J=5.9 Hz, 3H); LCMS (ESI, M): 661.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09409922B2 |
| Source dataset | uspto-grants-2016_08 |
| ORD ID | ord-b0f378895e5946eaa4e37e22f1674ec6 |
| Source note | uspto-grants-2016_08 |