Ethoxalyl chloride → HCID 59608116, compound

HRID 2384114Notes

Reaction equation

HRID 2384114 reaction equation
Cl.[NH2:2][C@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[CH:15][CH:14]=1)[CH2:4][CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[C:27](=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CN(C=O)C>[Cl:25][C:21]1[CH:20]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([CH2:12][C@@H:3]([NH:2][C:27](=[O:33])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:4][CH:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:18][CH:17]=2)[CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 67505770HCID 67505770, compound

Product 1

HCID 59608116HCID 59608116, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (4S)-ethyl 4-amino-5-(3′-chlorobiphenyl-4-yl)-2-methylpentanoate hydrochloride salt (600 mg, 1.74 mmol) in DMF (13.1 mL) is added TEA (0.25 mL, 1.82 mmol) and ethyl 2-chloro-2-oxoacetate (0.19 mL, 1.74 mmol) at room temperature. After stirring this reaction for 1 hour at room temperature, the reaction is quenched with H2O, and diluted in EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue is purified by flash column chromatography (eluent: heptane/EtOAc=70:30 to 50:50) to give (4S)-ethyl 5-(3′-chlorobiphenyl-4-yl)-4-(2-ethoxy-2-oxoacetamido)-2-methylpentanoate (637 mg). HPLC retention time=1.66 minutes (condition A); MS 446.5 (M+1).

Workup

  1. customthis reaction for 1 hour at room temperature
  2. customthe reaction is quenched with H2O
  3. additiondiluted in EtOAc
  4. washThe organic layer is washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue is purified by flash column chromatography (eluent: heptane/EtOAc=70:30 to 50:50)

Sources & evidence

ORD record
ord-55e02f7e86814329b79b24989d113407
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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