1,2-Dichloroethane → HCID 69220124, compound

HRID 1592775Notes

Reaction equation

HRID 1592775 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. concentrationdried Na2SO4) and concentrated to dryness
  3. 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-e053f4efe04f4908adc0a40797d83f99
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

Loading…