3,5-Dimethylbenzoyl Chloride → (R)-N'-(1-tert-butyl-but-3-enyl)-N'-(3,5-dimethyl-benzoyl)-hydrazinecarboxylic acid benzyl ester
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][NH:12][C@@H:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH:15]=[CH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([CH3:31])[CH:30]=1)[C:25](Cl)=[O:26]>>[CH2:1]([O:8][C:9]([NH:11][N:12]([C@@H:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:14][CH:15]=[CH2:16])[C:25](=[O:26])[C:24]1[CH:28]=[C:29]([CH3:31])[CH:30]=[C:22]([CH3:21])[CH:23]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
Briefly, benzyl carbazate (compound A) was reacted with pivaldehyde to give (E)-N′-(2,2-dimethyl-propylidene)-hydrazinecarboxylic acid benzyl ester (compound B). Compound B was reacted with (S,S)-2-allyl-2-chloro-3,4-dimethyl-5-phenyl-[1,3,2]oxazasilolidine (Compound C; see Leighton et al., J. Am. Chem. Soc. 125:9596 (2003) and WO 03/074534) to give (R)—N′-(1-tert-butyl-but-3-enyl)-hydrazinecarboxylic acid benzyl ester (compound D). Compound D was reacted with 3,5-dimethyl benzoyl chloride to give (R)—N′-(1-tert-butyl-but-3-enyl)-N′-(3,5-dimethyl-benzoyl)-hydrazinecarboxylic acid benzyl ester (compound B). Compound E was hydrogenated to give (R)-3,5-dimethyl-benzoic acid N-(1-tert-butyl-butyl)-hydrazide (compound F). Compound F was reacted with 2-ethyl-3-methoxybenzoyl chloride to give Compound 1. The crude material was triturated first with ether (2% ethanol) and then with 1:1 hexanes:ether in a fritted glass Büchner funnel. The product was then washed with deionized water with thorough mixing and allowed to dry in air. Compound 1 was isolated as a white powder.
Sources & evidence
- ORD record
- ord-ab77bf85e520448d89383523ebbdb90a
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946294B2
Reaction notes
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