1,2-Dichloroethane → HCID 131721918, compound

HRID 2269597Notes

Reaction equation

HRID 2269597 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([OH:9])=O)=[O:4].Cl.[NH2:21][C@H:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:24][CH2:25][CH3:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:2][C:3]([N:5]1[CH2:12][CH2:11][CH2:10][C@H:6]1[C:7]([NH:21][C@H:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:23][CH2:24][CH2:25][CH3:26])=[O:9])=[O:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 10464585HCID 10464585, compoundHCID 11673468Boc-gly-pro-OH

Product 1

HCID 131721918HCID 131721918, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Boc-Gly-Pro-OH (3.85 g, 0.014 mol), the HCl salt of Nleu-OEt (2.76 g, 0.014 mol) and HOBt (2.8 g, 0.02 mol.) were dissolved in 100 ml DMF and the solution was chilled to 0° C. on a water-ice bath. TEA (2.8 ml, 0.02 mol.) was added to the solution. After stirring the solution for 10 minutes, EDC (4.0 g, 0.021 mol.) was added. The stirring was continued overnight. The DMF was removed under reduced pressure and the resulting mixture was poured into 200 ml ethyl acetate. The organic layer was washed by H2O 2×30 ml, saturated NaHCO3 3×10 ml, brine 2×10 ml, saturated NaHSO4 3×15 ml and brine again until the pH value of the brine layer was approximately 7. The ethyl acetate solution was dried using Na2SO4 and the solvent was removed by distillation under reduced pressure. Column chromatography (elution solvents: E/H, 2:1) was performed to obtain the pure product (yellowish oil, 4.7 g, 81%). TLC Rf=0.54 (developing solvents: CMA, 85:15:3) and Rf=0.34 (developing solvents: E/H, 2:1).

Workup

  1. waitThe stirring was continued overnight
  2. customThe DMF was removed under reduced pressure
  3. additionthe resulting mixture was poured into 200 ml ethyl acetate
  4. washThe organic layer was washed by H2O 2×30 ml, saturated NaHCO3 3×10 ml, brine 2×10 ml, saturated NaHSO4 3×15 ml and brine again until the pH value of the brine layer
  5. dry with materialThe ethyl acetate solution was dried
  6. customthe solvent was removed by distillation under reduced pressure
  7. washColumn chromatography (elution solvents: E/H, 2:1)
  8. customto obtain the pure product (yellowish oil, 4.7 g, 81%)

Sources & evidence

ORD record
ord-d9852d9efca8474992d43c44cbd36d33
Source dataset
uspto-grants-2001_12
Patent number
US06329506B1

Reaction notes

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