Triethylamine → 2-[N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C:5]([N:8]([C:20](=[O:29])[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)[NH:9]C(OCC1C=CC=CC=1)=O)([CH3:7])[CH3:6])[CH3:2].CCN(CC)CC.[SiH](CC)(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:30])[C:5]([N:8]([C:20](=[O:29])[C:21]1[CH:22]=[C:23]([CH3:28])[CH:24]=[C:25]([CH3:27])[CH:26]=1)[NH2:9])([CH3:7])[CH3:6])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
Into a flask containing 1.5 g (0.0036 mol, 80% pure) of 2-[N′-benzyloxycarbonyl-N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester, was added 20 mL of dry CH2Cl2, 1.5 mL of Et3N, and 1.27 g(0.010 mol) of Et3SiH. While stirring, small portions of a total of 0.010 g of Pd(OAc)2 was added and the reaction was stirred for 2 hours at room temperature. To the reaction mixture was added 100 mL of CH2Cl2 and some MgSO4 to aid in the filtration/removal of the Pd product. The CH2Cl2 solution was shaken with saturated NH4Cl, CH2Cl2 dried, and evaporated to yield 1.61 g of 2-[N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester. The product was purified by chromatography, elution with 21-24% ethyl acetate in hexane. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.045 (s 2H), 7.0(s 1H), 4.4(s, 2H), 2.324(s 6H), 2.236(s 3H), 1.487(s, 6H).
Workup
- stirringthe reaction was stirred for 2 hours at room temperature
- customsome MgSO4 to aid in the filtration/removal of the Pd product
- stirringThe CH2Cl2 solution was shaken with saturated NH4Cl, CH2Cl2
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-a5cc5ba3fe5644aeb969547e4f1b6871
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07456315B2
Reaction notes
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