methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-(difluoromethyl)-17-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 → HCID 118316382, compound

HRID 1482146Notes

Reaction equation

HRID 1482146 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([CH:42]([F:44])[F:43])[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:50][CH2:49][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=2[C:30]2[CH:46]=[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]([CH:42]([F:43])[F:44])[C:38]2=[N:45][C:35]3=[CH:36][N:37]2[C:12]=1[N:13]1[CH2:14][CH2:15][C:16]([CH3:51])([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C@H:22]([CH3:48])[O:23][C:24]2[CH:25]=[CH:26][C:27]([F:47])=[CH:28][C:29]=2[C:30]2[CH:46]=[C:34]3[CH:33]=[CH:32][CH:31]=2)[CH2:49][CH2:50]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 118316380methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-(difluoromethyl)-17-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 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 118316382HCID 118316382, compoundYield 19.1%

Procedure

Prepared in 19.1% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-(difluoromethyl)-17-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 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 8.19 (s, 1H), 8.15 (d, J=7.7 Hz, 1H), 8.06 (s, 1H), 7.97-7.65 (m, 1H), 7.57-7.51 (m, 1H), 7.38 (d, J=7.7 Hz, 1H), 7.22 (d, J=7.3 Hz, 1H), 7.17 (d, J=4.8 Hz, 2H), 5.83 (br. s., 1H), 4.62 (br. s., 1H), 3.83 (br. s., 1H), 3.57 (d, J=11.7 Hz, 1H), 3.44 (d, J=9.2 Hz, 4H), 2.68 (d, J=10.6 Hz, 1H), 2.53 (br. s., 3H), 1.94-1.58 (m, 9H), 1.53 (br. s., 1H), 1.19 (s, 3H), 1.15 (s, 9H), 1.07 (d, J=5.9 Hz, 3H); LCMS (ESI, M+1): 678.3.

Sources & evidence

ORD record
ord-4bacf22c456d406494ffd0e0ac83fc4b
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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