2-Ethyl-3-methoxybenzoyl chloride → INXN-1001
Reaction equation
[C:1]([C@H:5]([N:9]([C:11](=[O:20])[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)[NH2:10])[CH2:6][CH2:7][CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([C:23]1[C:31]([O:32][CH3:33])=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26])[CH3:22]>>[C:1]([C@H:5]([N:9]([C:11](=[O:20])[C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1)[NH:10][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][CH:30]=[C:31]([O:32][CH3:33])[C:23]=1[CH2:21][CH3:22])[CH2:6][CH2:7][CH3:8])([CH3:4])([CH3:2])[CH3:3]Participants
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-10bd9a63c66f4dabb9fa90e99a2f3fc5
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946294B2
Reaction notes
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