O-(propan-2-yl)hydroxylamine hydrochloride → 6-[1-Hydroxy-1-(1H-imidazol-4-yl)-2-methylpropyl)-N-isopropoxy-2-naphthamide
Reaction equation
OC(C1C=C2C(=CC=1)C=C(C(OC)=O)C=C2)(C1N=CN(C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=1)C(C)C.[OH:44][C:45]([C:73]1[CH:74]=[C:75]2[C:80](=[CH:81][CH:82]=1)[CH:79]=[C:78]([C:83](O)=[O:84])[CH:77]=[CH:76]2)([C:49]1[N:50]=[CH:51][N:52](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:53]=1)[CH:46]([CH3:48])[CH3:47].Cl.[CH:87]([O:90][NH2:91])([CH3:89])[CH3:88]>>[OH:44][C:45]([C:73]1[CH:74]=[C:75]2[C:76](=[CH:81][CH:82]=1)[CH:77]=[C:78]([C:83]([NH:91][O:90][CH:87]([CH3:89])[CH3:88])=[O:84])[CH:79]=[CH:80]2)([C:49]1[N:50]=[CH:51][NH:52][CH:53]=1)[CH:46]([CH3:48])[CH3:47]Participants
4
Reactant 3
Product 1
Procedure
In a manner to that described in Example 9-(i), methyl 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoate (1.77 g) was converted to 6-(1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-2-naphthoic acid, which was reacted with O-isopropylhydroxylamine hydrochloride (420 mg) in a similar manner as described in Example 24-(i) to give the titled compound (1.46 g) as a pale yellow powder.
Sources & evidence
- ORD record
- ord-efa812c093f04884869dbb713a288bf5
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06649643B1
Reaction notes
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