Ethoxalyl chloride → HCID 59608116, compound

HRID 1469691Notes

Reaction equation

HRID 1469691 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-18a0660bc92c4344a33df81bb40f0c50
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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