Methyl(2S)-2-[(22S)-8-bromo-17-fluoro-4,18,22,28-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]-2-(tert-butoxy)acetate → (2S)-2-[(22S)-8-Bromo-17-fluoro-4,18,22,28-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]-2-(tert-butoxy)acetic acid

HRID 1482053Notes

Reaction equation

HRID 1482053 reaction equation
[Br:1][C:2]1[N:3]2[C:8]3[N:9]4[CH2:38][CH2:37][C:12]([CH3:39])([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]([CH3:36])[O:19][C:20]5[CH:21]=[C:22]([CH3:35])[C:23]([F:34])=[CH:24][C:25]=5[C:26]5[CH:33]=[C:30]([C:31]=1[N:32]=[C:4]2[CH:5]=[C:6]([CH3:50])[C:7]=3[C@H:40]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([O:43]C)=[O:42])[CH:29]=[CH:28][CH:27]=5)[CH2:11][CH2:10]4.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(O)=O)(C)(C)C>>[Br:1][C:2]1[N:3]2[C:8]3[N:9]4[CH2:10][CH2:11][C:12]([CH3:39])([O:13][CH2:14][CH2:15][CH2:16][CH2:17][C@H:18]([CH3:36])[O:19][C:20]5[CH:21]=[C:22]([CH3:35])[C:23]([F:34])=[CH:24][C:25]=5[C:26]5[CH:33]=[C:30]([C:31]=1[N:32]=[C:4]2[CH:5]=[C:6]([CH3:50])[C:7]=3[C@H:40]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[C:41]([OH:43])=[O:42])[CH:29]=[CH:28][CH:27]=5)[CH2:37][CH2:38]4

Participants

3

Reactant 2

HCID 118316304Methyl(2S)-2-[(22S)-8-bromo-17-fluoro-4,18,22,28-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]-2-(tert-butoxy)acetateHCID 123621546(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]acetic acid

Product 1

HCID 118316305(2S)-2-[(22S)-8-Bromo-17-fluoro-4,18,22,28-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]-2-(tert-butoxy)acetic acid

Procedure

Prepared in 24% from methyl(2S)-2-[(22S)-8-bromo-17-fluoro-4,18,22,28-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]-2-(tert-butoxy)acetate following the procedure for (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]acetic acid. 1H NMR (600 MHz, DMSO-d6) δ 8.09 (s, 1H), 7.73 (d, J=7.3 Hz, 1H), 7.56 (t, J=7.7 Hz, 1H), 7.43 (d, J=7.3 Hz, 1H), 7.33-7.29 (m, 1H), 7.14 (d, J=6.2 Hz, 1H), 7.04 (d, J=9.9 Hz, 1H), 5.75-5.61 (m, 1H), 4.69-4.59 (m, 1H), 4.31-2.61 (m, 6H), 2.43 (br. s., 3H), 2.27 (s, 3H), 1.94-1.39 (m, 10H), 1.20 (br. s., 3H), 1.15 (br. s., 9H), 1.08 (d, J=5.5 Hz, 3H); LCMS (ESI, M): 735.3.

Sources & evidence

ORD record
ord-fa7eb9f4d7be43e4b9fe93cedd375dd5
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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