(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-one → (R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one

HRID 385244Notes

Reaction equation

HRID 385244 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]=1[CH:14]=[CH:15][C:16](=[O:23])[NH:17]2)[O:4][Si](C(C)(C)C)(C)C.N(C[C@@H](C1C=CC(OCC2C=CC=CC=2)=C2C=1C=CC(=O)N2)O)=[N+]=[N-]>>[NH2:1][CH2:2][C@@H:3]([C:12]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]2[C:13]=1[CH:14]=[CH:15][C:16](=[O:23])[NH:17]2)[OH:4]

Participants

3

Reactant 2

HCID 58505170(R)-5-(2-Azido-1-hydroxyethyl)-8-(benzyloxy)quinolin-2(1H)-oneHCID 59023604(R)-5-(2-Amino-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-hydroxyquinolin-2(1H)-one

Product 1

HCID 24996153(R)-5-(2-Amino-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 2, using Intermediate 3 as a substrate. ES/MS calcd. for C11H13N2O3+ 221.1. found m/z=221.1 (M+H)+.

Sources & evidence

ORD record
ord-8aa1d9fd05c847c2aec89761e1a28221
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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