1,2-Dichloroethane → HCID 89157182, compound

HRID 1749071Notes

Reaction equation

HRID 1749071 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11](O)=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)CCl.C1C=[N:23]C2N(O)N=NC=2C=1.C(=O)([O-])O.[NH4+]>CN(C=O)C>[C:4]([O:3][C:1](=[O:2])[N:8]([C@H:9]([C:11](=[O:12])[NH2:23])[CH3:10])[CH3:14])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14013Ammonium BicarbonateHCID 181649HOAtHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Product 1

HCID 89157182HCID 89157182, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-N-methyl-L-alanine (3.12 g, 15.3 mmol), EDC (2.94 g, 15.3 mmol), HOAt (2.09 g, 15.3 mmol) and ammonium hydrogencarbonate (3.63 g, 45.9 mmol) were added to DMF (20 mL) and stirred at ambient temperature overnight. The mixture was partitioned between EtOAc and water. The EtOAc layer was washed with aqueous potassium hydrogen sulfate solution (×2), dilute aqueous sodium carbonate solution and brine. The EtOAc was evaporated to give the title compound as a white solid (1 g). 1H NMR (400 MHz, DMSO-d6): 7.19 (1H, br), 6.95 (1H, br), 4.60-4.20 (1H, m), 2.73 (3H, s), 1.39 (9H, s), 1.24 (3H, d).

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washThe EtOAc layer was washed with aqueous potassium hydrogen sulfate solution (×2), dilute aqueous sodium carbonate solution and brine
  3. customThe EtOAc was evaporated

Sources & evidence

ORD record
ord-877d2e22010c4fb1a41462d11e272bda
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

Loading…