(R)-N-[5-[2-Azido-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-(benzyloxy)phenyl]formamide → N-{5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-hydroxyphenyl}formamide

HRID 385251Notes

Reaction equation

HRID 385251 reaction equation
[NH2:1][CH2:2][C@@H:3]([C:12]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]2[C:13]=1C=C[C:16](=[O:23])[NH:17]2)[O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].N(C[C@@H](C1C=CC(OCC2C=CC=CC=2)=C(NC=O)C=1)O[Si](C(C)(C)C)(C)C)=[N+]=[N-]>>[NH2:1][CH2:2][C@@H:3]([C:12]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([NH:17][CH:16]=[O:23])[CH:13]=1)[O:4][Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

3

Reactant 2

HCID 58505165(R)-N-[5-[2-Azido-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-(benzyloxy)phenyl]formamideHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

Product 1

HCID 57461065N-{5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-hydroxyphenyl}formamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 2, using Intermediate 11 in place of Intermediate 1. ES/MS calcd. C15H27N2O3Si+ 311.2. found m/z=311 (M+H)+

Sources & evidence

ORD record
ord-6ef909a9009044469ebd45023a74f99c
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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