Triethylamine → HCID 59608173, compound

HRID 1469689Notes

Reaction equation

HRID 1469689 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]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:4][C@@H:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].Cl[C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)CC)C>CN(C=O)C>[C:16]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]([CH2:12][C@@H:3]([NH:2][C:26](=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:4][C@@H:5]([CH3:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chloride2×HCID 25017086(2R,4S)-4-amino-5-(biphenyl-4-yl)-2-methylpentanoic acid ethyl ester hydrochloride

Product 1

HCID 59608173HCID 59608173, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2R,4S)-ethyl 4-amino-5-(biphenyl-4-yl)-2-methylpentanoate hydrochloride salt (1 g, 2.87 mmol) in DMF (10 mL) is added TEA (0.42 mL, 3.02 mmol) followed by ethyl 2-chloro-2-oxoacetate (392 mg, 2.87 mmol). The crude is stirred at it for 1 hr. To the crude is added an additional 0.2 ml of ethyl 2-chloro-2-oxoacetate followed by triethylamine (1.26 mL, 9.06 mmol). The crude is quenched with water and diluted in EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated. The crude is purified via flash chromatography using 30% EtOAc/heptane to 50% EtOAc/heptane to give (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-ethoxy-2-oxoacetamido)-2-methylpentanoate (970 mg).

Workup

  1. customThe crude is quenched with water
  2. additiondiluted in EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude is purified via flash chromatography

Sources & evidence

ORD record
ord-10ec01cb640542cab1b0b2c8835473e5
Source dataset
uspto-grants-2015_04
Patent number
US09006249B2

Reaction notes

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