Methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-17-fluoro-5-(hydroxymethyl)-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 118316381, compound

HRID 1482145Notes

Reaction equation

HRID 1482145 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:40]([CH3:41])=[C:39]([CH2:42][OH:43])[C:38]2=[N:44][C:35]3=[C:36]([Cl:45])[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]([CH2:42][OH:43])[C:38]2=[N:44][C:35]3=[C:36]([Cl:45])[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 118316378Methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-17-fluoro-5-(hydroxymethyl)-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 118316381HCID 118316381, compoundYield 17.4%

Procedure

Prepared in 17.4% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-17-fluoro-5-(hydroxymethyl)-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 8.33 (s, 1H), 7.90 (d, J=7.7 Hz, 1H), 7.60 (t, J=7.5 Hz, 1H), 7.47 (d, J=7.7 Hz, 1H), 7.25 (s, 2H), 7.20-7.13 (m, 3H), 7.05 (s, 1H), 5.96 (br. s., 1H), 5.01-4.95 (m, 1H), 4.93-4.88 (m, 1H), 4.61 (br. s., 1H), 4.05-3.90 (m, 2H), 3.52 (br. s., 1H), 3.38 (br. s., 2H), 2.46 (br. s., 3H), 2.35 (br. s., 1H), 2.02-1.59 (m, 8H), 1.21 (br. s., 3H), 1.19 (s, 9H), 1.04 (d, J=5.9 Hz, 3H); LCMS (ESI, M+1): 708.1.

Sources & evidence

ORD record
ord-794ac51b05bd4e6bb06d966cc027e212
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

Loading…