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-decaen-3-yl]acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-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

HRID 1482107Notes

Reaction equation

HRID 1482107 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[CH:39][C:38]2=[N:42][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:48][CH2:47][C:16]([CH3:49])([O:17][CH2:18][CH:19]=[CH:20][CH2:21][C@H:22]([CH3:46])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:45])=[C:28]([F:44])[C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCCCC[C@H](C)OC2C=C(F)C=CC=2C2C=C3C=CC=2)CC1)C(OC)=O)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[CH:39][C:38]2=[N:42][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:14][CH2:15][C:16]([CH3:49])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:46])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:45])=[C:28]([F:44])[C:29]=2[C:30]2[CH:43]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:47][CH2:48]1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 118316270Methyl(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-decaen-3-yl]acetateHCID 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]acetate

Product 1

HCID 118316344Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-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]acetateYield 69.8%

Procedure

Prepared in 69.8% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S,24Z)-16,17-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),16,18,24-undecaen-3-yl]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-decaen-3-yl]acetate. 1H NMR (500 MHz, CDCl3) δ 8.21 (dt, J=7.9, 1.3 Hz, 1H), 8.01 (s, 1H), 7.90 (t, J=1.5 Hz, 1H), 7.56 (t, J=7.7 Hz, 1H), 7.38-7.33 (m, 2H), 7.14-7.06 (m, 1H), 6.72-6.68 (m, 1H), 6.07 (br. s., 1H), 4.51-4.45 (m, 1H), 4.04-3.95 (m, 1H), 3.77 (t, J=10.8 Hz, 1H), 3.71 (s, 3H), 3.56-3.50 (m, 1H), 3.50-3.45 (m, 1H), 3.09 (d, J=10.1 Hz, 1H), 2.71 (d, J=7.7 Hz, 1H), 2.48 (d, J=0.9 Hz, 3H), 2.00-1.92 (m, 2H), 1.85-1.71 (m, 8H), 1.30 (s, 3H), 1.27 (s, 9H), 1.13 (d, J=6.1 Hz, 3H); LCMS (ESI, M+1): 676.80.

Sources & evidence

ORD record
ord-282ee48928f542ea9848519f928192a2
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…