(R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-bromoethanol → (R)-1-(3-Amino-4-(benzyloxy)phenyl)-2-azidoethanol

HRID 385253Notes

Reaction equation

HRID 385253 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=CC(=O)[NH:19]2)[O:6][Si](C(C)(C)C)(C)C)=[N+:2]=[N-:3].NC1C=C([C@@H](O)CBr)C=CC=1OCC1C=CC=CC=1>>[NH2:19][C:20]1[CH:15]=[C:14]([C@@H:5]([OH:6])[CH2:4][N:1]=[N+:2]=[N-:3])[CH:23]=[CH:22][C:21]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 11232489(R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-bromoethanolHCID 58505233(R)-5-(2-Azido-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H)-one

Product 1

HCID 57516929(R)-1-(3-Amino-4-(benzyloxy)phenyl)-2-azidoethanol

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 1, using Intermediate 13 in place of (R)-8-(benzyloxy)-5-[2-bromo-1-[(tert-butyldimethylsilyl)oxy]ethyl]quinolin-2(1H)-one. ES/MS calcd. for C15H17N4O2+ 285.1. found m/z=285 (M+H)+.

Sources & evidence

ORD record
ord-ca1fe8518ed244528c31c3a40eed3069
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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