Triethylamine → 2-[N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester

HRID 39657Notes

Reaction equation

HRID 39657 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

6

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 598386122-[N'-Benzyloxycarbonyl-N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester

Product 1

HCID 598385882-[N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl esterYield 160.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent2×

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 31-1), 1.487 (s, 6H).

Workup

  1. stirringthe reaction was stirred for 2 hours at room temperature
  2. customsome MgSO4 to aid in the filtration/removal of the Pd product
  3. stirringThe CH2Cl2 solution was shaken with saturated NH4Cl, CH2Cl2
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-2c4c1c7054454bd0bc021f154264b68e
Source dataset
uspto-grants-2013_09
Patent number
US08524948B2

Reaction notes

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