Benzoyl chloride → 3-Benzoylamino-2-methyl-butyric acid, ethyl ester

HRID 1888119Notes

Reaction equation

HRID 1888119 reaction equation
[NH2:1][CH:2]([CH3:10])[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCCCCC.CCOC(C)=O>ClCCl>[C:18]([NH:1][CH:2]([CH3:10])[CH:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10341339Ethyl 3-amino-2-methylbutanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 5699253-Benzoylamino-2-methyl-butyric acid, ethyl esterYield 25.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 3-amino-2-methylbutanoate (0.15 g, 1.033 mmol) in dichloromethane (3 mL) was added triethylamine (0.288 mL, 2.066 mmol) followed by the dropwise addition of benzoyl chloride (0.120 mL, 1.033 mmol) at RT. The reaction mixture was stirred at RT for 1 h, partitioned between dichloromethane (20 mL) and 1N HCL (10 mL). The dichloromethane layer was washed with 1N NaOH (10 mL), brine (10 mL), dried over sodium sulfate and concentrated to yield an oil. The oil was subjected to silica gel chromatography using an ISCO setup (12 g silica gel RediSep cartridge, hexane/EtOAc as eluent). The desired fractions are collected and concentrated to yield the title compound (0.066 g, 0.265 mmol, 25.6% yield) as an oil.

Workup

  1. custompartitioned between dichloromethane (20 mL) and 1N HCL (10 mL)
  2. washThe dichloromethane layer was washed with 1N NaOH (10 mL), brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe desired fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-49dc8b551a7b4f278ce55c4f75673152
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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