(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2',3'-difluoro-6'-((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,24Z)-16,17-difluoro-4,22,28-trim ethyl-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 1482106Notes

Reaction equation

HRID 1482106 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[C:31]([O:32][C@H:33]([CH2:35][CH:36]=C)[CH3:34])=[CH:30][CH:29]=[C:28]([F:38])[C:27]=5[F:39])[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]=C.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[CH2:7][CH2:6][C:5]([CH3:51])([O:4][CH2:1][CH:2]=[CH:36][CH2:35][C@H:33]([CH3:34])[O:32][C:31]2[CH:30]=[CH:29][C:28]([F:38])=[C:27]([F:39])[C:26]=2[C:22]2[CH:21]=[C:20]3[CH:25]=[CH:24][CH:23]=2)[CH2:10][CH2:9]1)[C:42]([O:44][CH3:45])=[O:43])([CH3:48])([CH3:49])[CH3:50]

Participants

3

Reactant 2

HCID 118308868(S)-Methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2',3'-difluoro-6'-((S)-pent-4-en-2-yloxy)-[1,1'-biphenyl]-3-yl)-7-methylimidazo[1,2-a]pyridin-6-yl)-2-(tert-butoxy)acetateHCID 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 118316342Methyl(2S)-2-(tert-butoxy)-2-[(22S,24Z)-16,17-difluoro-4,22,28-trim ethyl-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 81%

Procedure

Prepared in 81.0% yield from (S)-methyl 2-(5-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(2′,3′-difluoro-6′-((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. LCMS (ESI, M+1): 674.6.

Sources & evidence

ORD record
ord-2cd87f54b4bf452fba4846c269f30132
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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