(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamide → (R)-N-[5-(2-Azido-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide

HRID 1944849Notes

Reaction equation

HRID 1944849 reaction equation
[N:1]([CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:20]2[C:15]=1C=C[C:18](=[O:32])[NH:19]2)[O:6][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].C(OC1C=CC([C@@H](O)CBr)=CC=1NC=O)C1C=CC=CC=1>>[N:1]([CH2:4][C@@H:5]([C:14]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:20]([NH:19][CH:18]=[O:32])[CH:15]=1)[OH:6])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 58505134(R)-N-[5-(2-Azido-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 1, using Intermediate 10 as a substrate. ES/MS calcd. C16H17N4O3+ 313.1. Found m/z=313 (M+H)+.

Sources & evidence

ORD record
ord-e03cf3a47684410a98086c6789162ffe
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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