(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-dimethyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-4,17,18,22,28-pentamethyl-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

HRID 1482030Notes

Reaction equation

[CH2:1]([O:4][C:5]1([CH3:51])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[CH:17]=[C:18]([C:20]4[CH:21]=[C:22]([C:26]5[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=5[O:34][C@H:35]([CH2:37]C=C)[CH3:36])[CH:23]=[CH:24][CH:25]=4)[N:19]=[C:15]3[CH:14]=[C:13]([CH3:40])[C:12]=2[C@H:41]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:42]([O:44][CH3:45])=[O:43])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCC=CC[C@H](C)OC2C=C(F)C=CC=2C2C=C3C=CC=2)CC1)C(OC)=O)(C)(C)C>>[C:47]([O:46][C@@H:41]([C:12]1[C:13]([CH3:40])=[CH:14][C:15]2=[N:19][C:18]3=[CH:17][N:16]2[C:11]=1[N:8]1[CH2:9][CH2:10][C:5]([CH3:51])([O:4][CH2:1][CH:2]=[CH:3][CH2:36][C@H:35]([CH3:37])[O:34][C:27]2[CH:28]=[C:29]([CH3:33])[C:30]([CH3:32])=[CH:31][C:26]=2[C:22]2[CH:21]=[C:20]3[CH:25]=[CH:24][CH:23]=2)[CH2:6][CH2:7]1)[C:42]([O:44][CH3:45])=[O:43])([CH3:48])([CH3:50])[CH3:49]

Participants

Reactant 2

HCID 118308926(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4',5'-dimethyl-2'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate

HCID 123468036Methyl(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]acetate

Product 1

HCID 131736662Methyl(2S)-2-(tert-butoxy)-2-[(22S)-4,17,18,22,28-pentamethyl-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]acetateYield 80%

Procedure

Prepared in 80% yield from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(4′,5′-dimethyl-2′-((S)-pent-4-en-2-yloxy)-[1,1′-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetate following the procedure for methyl(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]acetate. 1H NMR (400 MHz, CDCl3) δ 8.14 (d, J=7.8 Hz, 1H), 8.07 (s, 1H), 8.03 (s, 1H), 7.55-7.47 (m, 1H), 7.35-7.29 (m, 2H), 7.12 (s, 1H), 6.84 (s, 1H), 6.26-6.14 (m, 1H), 6.06 (br. s., 1H), 5.89-5.74 (m, 1H), 4.57-4.44 (m, 1H), 4.10-4.05 (m, 1H), 4.03-3.93 (m, 2H), 3.84-3.73 (m, 1H), 3.69 (s, 3H), 3.07 (d, J=8.3 Hz, 1H), 2.68 (d, J=7.5 Hz, 1H), 2.51 (br. s., 1H), 2.46 (s, 3H), 2.43-2.34 (m, 1H), 2.31 (s, 3H), 2.25 (s, 3H), 1.97 (t, J=12.5 Hz, 2H), 1.75 (td, J=12.9, 4.5 Hz, 2H), 1.32 (s, 3H), 1.25 (s, 9H), 1.10 (d, J=6.3 Hz, 3H); LCMS (ESI, M+1): 666.3.

Sources & evidence

ORD record: ord-d0b88e48fa8742f891e9253fa581019f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

Loading…