(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one → (R)-N-[5-[2-Amino-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-hydroxyphenyl]methanesulfonamide

HRID 1944854Notes

Reaction equation

HRID 1944854 reaction equation
NC[C@@H](C1C=CC(O)=C2C=1C=CC(=O)N2)O[Si](C(C)(C)C)(C)C.[N:24]([CH2:27][C@@H:28]([C:37]1[CH:38]=[CH:39][C:40]([O:48]CC2C=CC=CC=2)=[C:41]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])[CH:42]=1)[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[N+]=[N-]>>[NH2:24][CH2:27][C@@H:28]([C:37]1[CH:38]=[CH:39][C:40]([OH:48])=[C:41]([NH:43][S:44]([CH3:47])(=[O:45])=[O:46])[CH:42]=1)[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-oneHCID 86659064(R)-N-[5-[2-Azido-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-(benzyloxy)phenyl]methanesulfonamide

Product 1

HCID 66989965(R)-N-[5-[2-Amino-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-hydroxyphenyl]methanesulfonamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 2, using Intermediate 17 in place of Intermediate 1. The compound was used with no further purification. ES/MS calcd. for C15H29N2O4SSi+ 361.2. Found m/z=361 (M+H)+.

Workup

  1. customThe compound was used with no further purification

Sources & evidence

ORD record
ord-64317a2bace44120b01a12a591c17421
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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