(R)-1-[4-(Benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-bromoethanol → (R)-N-[5-[2-Azido-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-(benzyloxy)phenyl]formamide

HRID 385250Notes

Reaction equation

HRID 385250 reaction equation
C(OC1C=CC([C@@H](O)CBr)=CC=1CO[Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])C1C=CC=CC=1.[N:28]([CH2:31][C@@H:32]([C:34]1[CH:35]=[CH:36][C:37]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[C:38]([NH:40][CH:41]=[O:42])[CH:39]=1)[OH:33])=[N+:29]=[N-:30]>>[N:28]([CH2:31][C@@H:32]([C:34]1[CH:35]=[CH:36][C:37]([O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[C:38]([NH:40][CH:41]=[O:42])[CH:39]=1)[O:33][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[N+:29]=[N-:30]

Participants

3

Reactant 2

HCID 58505102(R)-1-[4-(Benzyloxy)-3-[[(tert-butyldimethylsilyl)oxy]methyl]phenyl]-2-bromoethanolHCID 58505134(R)-N-[5-(2-Azido-1-hydroxyethyl)-2-(benzyloxy)phenyl]formamide

Product 1

HCID 58505165(R)-N-[5-[2-Azido-1-[(tert-butyldimethylsilyl)oxy]ethyl]-2-(benzyloxy)phenyl]formamide

Procedure

The title compound was synthesized in a manner analogous to that described for Intermediate 5, using Intermediate 10 in place of (R)-4-(2-bromo-1-hydroxyethyl)-2-(hydroxymethyl)phenol. ES/MS calcd. C22H31N4O3Si+ 427.2. found m/z=427 (M+H)+.

Sources & evidence

ORD record
ord-1ca70cbc4b5f4e49b799f1b54182765f
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

Loading…