Benzoyl chloride → HCID 20658017, compound

HRID 1979264Notes

Reaction equation

HRID 1979264 reaction equation
[NH2:1][CH2:2][CH2:3][C@@H:4]([C@@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(CC)CC)C.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCl>[C:27]([NH:1][CH2:2][CH2:3][C@@H:4]([C@@H:12]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]([OH:15])=[O:14])[C:5]([O:7][C:8]([CH3:10])([CH3:11])[CH3:9])=[O:6])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 20658011HCID 20658011, compound

Product 1

HCID 20658017HCID 20658017, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.0 g of 2(R)-[3-amino-1(S)-(tert-butoxycarbonyl)propyl]-4-methylvaleric acid in 20 ml of dichloromethane was cooled to 5° C. under nitrogen and treated with 1.3 ml of triethylamine and a solution of 0.54 g of benzoyl chloride in 10 ml of dichloromethane. The mixture was stirred overnight at room temperature and then the solvent was evaporated. The residue was dissolved in ethyl acetate and washed with 2M aqueous hydrogen chloride and water. Drying over anhydrous magnesium sulfate, filtration and evaporation of the solvent gave a pale yellow oil which was purified by flash column chromatography on silica gel, using ethyl acetate/hexane (3:1), to give 0.78 g of 2(R)-[3-benzamido-1(S)-(tert-butoxycarbonyl)propyl]-4-methylvaleric acid in the form of a colorless oil.

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with 2M aqueous hydrogen chloride and water
  4. dry with materialDrying over anhydrous magnesium sulfate, filtration and evaporation of the solvent
  5. customgave a pale yellow oil which
  6. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-ec0171269fb44c1098f5c2df204ccfb6
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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