1,2-Dichloroethane → HCID 69220124, compound

HRID 456485Notes

Reaction equation

HRID 456485 reaction equation
[NH2:1][C@@H:2]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[CH:15]1[CH:16]=[CH:17][C:18]2N(O)N=N[C:19]=2[CH:20]=1.CC[N:27]([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29].C(Cl)CCl.C(Cl)Cl.CN(C=[O:45])C>CCOC(C)=O>[CH3:14][O:13][C:11](=[O:12])[CH:2]([NH:1][C:29]([CH:28]1[CH2:30][C:18]2[C:19](=[CH:20][CH:15]=[CH:16][CH:17]=2)[C:31]([CH3:33])([CH3:32])[NH:27]1)=[O:45])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8274224-Chloro-d-phenylalanine methyl esterHCID 22350042dichloromethane N,N-dimethylformamide

Product 1

HCID 69220124HCID 69220124, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dimethyl Tic (240 mg, 1.17 mmol), 4-Cl-D-Phe-OMe (322 mg, 1.28 mmol), HOBT (197 mg, 1.46 mmol), and DIPEA (0.81 mL, 44.68 mmol) in DCM/DMF (1:1) was added EDC (280 mg, 1.46 mmol). The resulting mixture was stirred at r.t. overnight. The mixture was then diluted with EtOAc (100 mL), washed with saturated aqueous NaHCO3 and brine, and then dried (Na2SO4) and concentrated to dryness. Purification and separation of diastereomers by flash chromatography (35 g SiO2, linear gradient, 40 mL/min 10–50% EtOAc/hexane for 25 minutes and 50% EtOAc/hexane for 7 minutes) afforded the final compound. LRMS (ESI+): 401.1 (M+H)

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to dryness
  4. customPurification and separation of diastereomers by flash chromatography (35 g SiO2, linear gradient, 40 mL/min 10–50% EtOAc/hexane for 25 minutes and 50% EtOAc/hexane for 7 minutes)

Sources & evidence

ORD record
ord-b3da344b214c4f63893c63946c3b20d8
Source dataset
uspto-grants-2007_03
Patent number
US07186715B2

Reaction notes

Loading…