1,2-Dichloroethane → HCID 86644350, compound

HRID 336449Notes

Reaction equation

HRID 336449 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@:4]([NH2:16])([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][C:6]([OH:8])=[O:7].C(N(CC)CC)C.[CH:25](O)([CH3:27])[CH3:26].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@:4]([NH2:16])([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:5][C:6]([O:8][CH:25]([CH3:27])[CH3:26])=[O:7]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3776IsopropanolHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86644351HCID 86644351, compound

Product 1

HCID 86644350HCID 86644350, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Commercially available (S)-2-BOC-amino-succinic acid 1-methyl ester (2.4 g, 10 mmol) was dissolved in DCM (30 mL), and triethylamine (2.8 mL, 20 mmol) was added thereto. To the mixture were added isopropanol (660 mg, 11 mmol), EDC (2.5 g, 26 mmol) and HOBt (2.3 g, 30 mmol), and the mixture was stirred for 4 h at room temperature. The reaction was quenched by saturated aqueous NaHCO3 solution. The reaction mixture was extracted with EtOAc, washed with saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give the title compound (2.5 g, Yield 87%).

Workup

  1. customThe reaction was quenched by saturated aqueous NaHCO3 solution
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a753946aebd3485c9c9ca0f2852f7339
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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