(R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenol → (R)-6-[[3-[[4-[[2-[3-[[(tert-Butyldimethylsilyl)oxy]methyl]-4-hydroxyphenyl]-2-hydroxyethyl]amino]piperidine-1-yl]carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

HRID 1944973Notes

Reaction equation

HRID 1944973 reaction equation
[Si](O[C@H](C1C=CC(O)=C2C=1C=CC(=O)N2)CN[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[CH:21]=[C:22]([S:26]([C:29]3[CH:30]=[C:31]4[C:36](=[C:37]([CH3:39])[CH:38]=3)[N:35]=[CH:34][C:33]([C:40]([NH2:42])=[O:41])=[C:32]4[NH:43][C:44]3[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH3:51])[CH:45]=3)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=2)=[O:19])[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.[NH2:64][CH2:65][C@@H:66]([C:68]1[CH:73]=[CH:72][C:71]([OH:74])=[C:70]([CH2:75][O:76][Si:77]([C:80]([CH3:83])([CH3:82])[CH3:81])([CH3:79])[CH3:78])[CH:69]=1)[OH:67]>>[Si:77]([O:76][CH2:75][C:70]1[CH:69]=[C:68]([C@@H:66]([OH:67])[CH2:65][NH:64][CH:12]2[CH2:17][CH2:16][N:15]([C:18]([C:20]3[CH:21]=[C:22]([S:26]([C:29]4[CH:30]=[C:31]5[C:36](=[C:37]([CH3:39])[CH:38]=4)[N:35]=[CH:34][C:33]([C:40]([NH2:42])=[O:41])=[C:32]5[NH:43][C:44]4[CH:49]=[CH:48][CH:47]=[C:46]([O:50][CH3:51])[CH:45]=4)(=[O:27])=[O:28])[CH:23]=[CH:24][CH:25]=3)=[O:19])[CH2:14][CH2:13]2)[CH:73]=[CH:72][C:71]=1[OH:74])([C:80]([CH3:83])([CH3:82])[CH3:81])([CH3:78])[CH3:79]

Participants

3

Reactant 2

HCID 58505193(R)-4-(2-Amino-1-hydroxyethyl)-2-[[(tert-butyldimethylsilyl)oxy]methyl]phenolHCID 66988139(R)-6-[[3-[[4-[[2-[(Tert-Butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]piperidin-1-yl]carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Product 1

HCID 66988921(R)-6-[[3-[[4-[[2-[3-[[(tert-Butyldimethylsilyl)oxy]methyl]-4-hydroxyphenyl]-2-hydroxyethyl]amino]piperidine-1-yl]carbonyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 150, using Intermediate 9 in place of Intermediate 2. ES/MS calcd. for C45H56N5O8SSi+ 854.4. Found m/z=854 (M+H)+.

Sources & evidence

ORD record
ord-65d23bd296ad4bf9a5dcaea7139c5bfa
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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