1-Chloro-3-iodopropane → Methyl 2-hydroxy-2-(4-methoxyphenyl)acetate
Reaction equation
ClCCC[C:5]([O:18]C)([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].COC(C1C=CC(OC)=CC=1)C(OC)=O.ClCCCI>>[OH:18][CH:5]([C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:6]([O:8][CH3:9])=[O:7]Participants
4
Procedure
246 mg of a mixture of methyl 5-chloro-2-methoxy-2-(4-methoxyphenyl)valerate with methyl methoxy-(4-methoxyphenyl)acetate was obtained from methyl hydroxy-(4-methoxyphenyl)acetate (724 mg) and 1-chloro-3-iodopropane (0.56 ml) by the same method as in Examples 85 and 86. Then, the ester mixture was hydrolyzed and amidated with tert-butyl carbazate according to the method in Examples 85 and 86 to obtain 32 mg of tert-butyl N′-[5-chloro-2-methoxy-2-(4-methoxyphenyl)pentanoyl]hydrazinecarboxylate and 122 mg of tert-butyl N′-[2-methoxy-2-(4-methoxyphenyl)acetyl]hydrazinecarboxylate.
Sources & evidence
- ORD record
- ord-1ddb5f626ee14ed798ea1730311faad3
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07713993B2
Reaction notes
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