methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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

HRID 1482079Notes

Reaction equation

HRID 1482079 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)[C:38]2=[N:48][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:53][CH2:52][C:16]([CH3:54])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:51])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:50])=[CH:28][C:29]=2[C:30]2[CH:49]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14]1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C)=CC2=NC3=C(Cl)N2C=1N1CCC(C)(OCCCC[C@H](C)OC2C=CC(C)=CC=2C2C=C3C=CC=2)CC1)C(O)=O)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([C:42]2[CH:43]=[CH:44][N:45]=[CH:46][CH:47]=2)[C:38]2=[N:48][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:14][CH2:15][C:16]([CH3:54])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:51])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:50])=[CH:28][C:29]=2[C:30]2[CH:49]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:52][CH2:53]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 118316326methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 118332041(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

Product 1

HCID 118316327(2S)-2-(tert-Butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 acidYield 27.2%

Procedure

Prepared in 27.2% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-5-(pyridin-4-yl)-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 (500 MHz, DMSO-d6) δ 8.70 (d, J=5.5 Hz, 2H), 8.13 (s, 1H), 8.05 (s, 1H), 7.87 (d, J=7.7 Hz, 1H), 7.45 (d, J=5.5 Hz, 3H), 7.31 (d, J=7.7 Hz, 1H), 7.22-7.12 (m, 3H), 5.91 (br. s., 1H), 4.60 (br. s., 1H), 3.92-3.81 (m, 1H), 3.62 (d, J=12.1 Hz, 1H), 3.44 (br. s., 4H), 2.19 (s, 3H), 1.93-1.65 (m, 9H), 1.54 (br. s., 1H), 1.20 (s, 3H), 1.18 (s, 9H), 1.06 (d, J=6.2 Hz, 3H). LCMS (ESI, M): 720.4.

Sources & evidence

ORD record
ord-2636aa633abd4b97a1e93f8f20db14ca
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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