1,2-Dichloroethane → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)-1-(1H-indol-3-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 2223246Notes

Reaction equation

HRID 2223246 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][NH:24]1.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.C(Cl)CCl>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:20]([N:24]1[CH2:25][CH2:26][C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23]1)=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 70461,2,3,4-TetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 178418300HCID 178418300, compound

Product 1

HCID 69900649[2-(3,4-Dihydro-1H-isoquinolin-2-yl)-1-(1H-indol-3-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyloxycarbonyl-L-tryptophan (3.00 g, 9.9 mmol) and 1,2,3,4-tetrahydroisoquinoline (1.31 g, 9.9 mmol) were suspended in THF (20 ml). At a temperature of 0° C., hydroxybenzotriazole (1.33 g, 9.9 mmol), diisopropylethylamine (1.27 g, 9.9 mmol), and EDC (N-3-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride, 1.89 g, 9.9 mmol) were added. The reaction mixture was stirred overnight at r.t. The solvent was evaporated, the residue was taken up in ethyl acetate, washed with water, and dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=420.5 (M+H+), (2.90 g, 70%) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

Workup

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-3b7b631a0825407d8466ed1fdd2dc211
Source dataset
uspto-grants-2008_05
Patent number
US07375099B2

Reaction notes

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