Triethylamine → HCID 68825048, compound

HRID 1986591Notes

Reaction equation

HRID 1986591 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH3:28][O:29][C:30]1[C:31]([O:50][CH3:51])=[CH:32][C:33]2[CH2:34][CH:35]3[CH2:49][NH:48][CH2:47][CH2:46][N:36]3[CH:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:38]=2[CH:39]=1>O1CCCC1.C(Cl)Cl>[CH3:28][O:29][C:30]1[C:31]([O:50][CH3:51])=[CH:32][C:33]2[CH2:34][CH:35]3[CH:49]([C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[NH:48][CH2:47][CH2:46][N:36]3[CH:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:38]=2[CH:39]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 9883736HCID 9883736, compound

Product 1

HCID 68825048HCID 68825048, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

2-[(tert-Butoxy)carbonylamino]acetic acid (1 g) is dissolved in tetrahydrofuran (4 ml), and thereto are added dropwise triethylamine (0.8 ml) and isobutyl chloroformate (0.8 ml) at −20° C., and the mixture is stirred at −10° C. for 5 minutes. To the mixture is added dropwise a suspension of 8,9-dimethoxy-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline (the compound obtained in Example 1-(6)) (1.6 g) in methylene chloride (15 ml), and the mixture is stirred at room temperature overnight. The reaction solution is concentrated under reduced pressure, and extracted with methylene chloride. The extract is washed with a saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=4:1) to give 8,9-dimethoxy-2-(tert-butoxycarbonyl)aminoacetyl-6-phenyl-1,3,4,6,11,11a-hexahydro-2H-pyrazino[1,2-b]isoquinoline (872 mg).

Workup

  1. additionTo the mixture is added dropwise
  2. stirringthe mixture is stirred at room temperature overnight
  3. concentrationThe reaction solution is concentrated under reduced pressure
  4. extractionextracted with methylene chloride
  5. washThe extract is washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by column chromatography on silica gel (eluent; chloroform:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-7ed5fee44c414304890961a5fc99c443
Source dataset
uspto-grants-2009_06
Patent number
US07550464B2

Reaction notes

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