1,2-Dichloroethane → HCID 131721923, compound

HRID 2269601Notes

Reaction equation

HRID 2269601 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([OH:13])=O)[CH2:7][CH2:8][CH2:9][CH3:10])=[O:4].Cl.[NH:22]1[CH2:37][CH2:36][CH2:35][C@H:23]1[C:24]([O:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])=[O:25].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.C(N(CC)CC)C>[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][C:3]([NH:5][C@H:6]([C:11]([N:22]1[CH2:37][CH2:36][CH2:35][C@H:23]1[C:24]([O:26][C:27]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:28])=[O:25])=[O:13])[CH2:7][CH2:8][CH2:9][CH3:10])=[O:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 57194832HCID 57194832, compoundHCID 131721921HCID 131721921, compound

Product 1

HCID 131721923HCID 131721923, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Boc-Gly-Nleu-OH (12.5 g, 0.043 mol.), HCl.Pro-OBz (11 g, 0.046 mol.) and HOBt (6.0 g, 0.045 mol.) were dissolved in 300 ml DMF and the solution was chilled to 0° C. Triethylamine (12 ml) was added slowly while stirring the solution. After 5 minutes, EDC (8.5 g, 0.043 mol.) was added to the solution and the stirring was continued at room temperature overnight. The DMF was removed under reduced pressure and the resulting mixture was poured into 350 ml ethyl acetate. The ethyl acetate solution was washed by H2O, saturated NaHCO3, brine, saturated NaHSO4 and brine again until the pH of the brine layer was about 7. The organic layer was dried by Na2SO4 and the ethyl acetate was removed under reduced pressure to get the crude product. Column chromatography (elution solvents: E/H, 3:1) was carried out to obtain the pure product (17.5 g, 85%). TLC Rf=0.45 (developing solvents: E/H, 3:1).

Workup

  1. waitthe stirring was continued at room temperature overnight
  2. customThe DMF was removed under reduced pressure
  3. additionthe resulting mixture was poured into 350 ml ethyl acetate
  4. washThe ethyl acetate solution was washed by H2O, saturated NaHCO3, brine, saturated NaHSO4 and brine again until the pH of the brine layer
  5. dry with materialThe organic layer was dried by Na2SO4
  6. customthe ethyl acetate was removed under reduced pressure
  7. customto get the crude product
  8. washColumn chromatography (elution solvents: E/H, 3:1)

Sources & evidence

ORD record
ord-6d2fff9ec1c844c88230cb5dd86588a5
Source dataset
uspto-grants-2001_12
Patent number
US06329506B1

Reaction notes

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