1,2-Dichloroethane → HCID 53737479, compound

HRID 1675182Notes

Reaction equation

HRID 1675182 reaction equation
[C:1]([O:5][C:6](NCC(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Cl)CCl.C1C=NC2N(O)N=[N:33][C:27]=2[CH:26]=1.CN(C=[O:39])C>>[CH2:13]([N:20]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:26](=[O:39])[CH2:27][NH2:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 7504BenzylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 181649HOAt

Product 1

HCID 53737479HCID 53737479, compound

Conditions

Temperature
0 °C

Procedure

To a solution of N-(tert-butoxycarbonyl)glycine (20.00 g, 114.16 mmol) in DMF (75 mL) was added benzylamine (24.9 mL, 228.32 mmol). The solution was cooled to 0° C. and treated with EDC (43.77 g, 228.32 mmol) and HOAT (15.54 g, 114.16 mmol). The reaction was stirred at 0° C. for 10 min and at rt for 2 h. The solvent was removed in vacuo, and the resulting residue was partitioned between EtOAc, ice water, and saturated aqueous NaHCO3 solution. The layers were separated, and the organic extract was washed twice with water, once with 10% aqueous KHSO4 solution, twice more with water, and once with brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford the product as a white solid 1H NMR (400 MHz, CDCl3) δ 7.35-7.26 (m, 5H), 6.44 (br s, 1H), 5.14 (br s, 1H), 4.46 (d, J=6.0 Hz, 2H), 3.83 (d, J=6.0 Hz, 2H), 1.43 (s, 9H); ES MS (M+23)=287.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was partitioned between EtOAc, ice water, and saturated aqueous NaHCO3 solution
  3. customThe layers were separated
  4. extractionthe organic extract
  5. washwas washed twice with water, once with 10% aqueous KHSO4 solution, twice more with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68db5c2c97544a70bea1cd91e4a1da7f
Source dataset
uspto-grants-2011_08
Patent number
US08003653B2

Reaction notes

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