1,2-Dichloroethane → HCID 131733309, compound

HRID 515888Notes

Reaction equation

HRID 515888 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([CH2:18][C:19]([OH:21])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(N(CC)CC)C.C(Cl)CCl.OC1C2N=NNC=2C=CC=1>ClCCl>[O:25]1[CH2:26][CH2:27][N:22]([C:19](=[O:21])[CH2:18][C@@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:23][CH2:24]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 2761615[(3S)-2-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl]acetic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 131733309HCID 131733309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3 g (10.30 mmol) of [(3S)-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-3-yl]acetic acid in 100 mL of dichloromethane, there are added dropwise 1.10 mL (11.32 mmol) of morpholine, still dropwise 4.3 mL (30.9 mmol) of triethylamine, 2.20 g (12.40 mmol) of EDC and 1.70 g (1.68 mmol) of HOBt (hydroxybenzotriazole). The batch is stirred at ambient temperature for 15 hours. The reaction mixture is then diluted with dichloromethane, successively washed with 1M HCl solution, saturated aqueous NaHCO3 solution and then brine until neutral. The organic phase is then dried over MgSO4, filtered and concentrated to dryness. After purification by chromatography over silica gel using dichloromethane and methanol as eluants, the title product is obtained in the form of an oil.

Workup

  1. washsuccessively washed with 1M HCl solution, saturated aqueous NaHCO3 solution
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customAfter purification by chromatography over silica gel

Sources & evidence

ORD record
ord-b0774e467c5149a5a1779485a04ee4f5
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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