Triethylamine → HCID 59323111, compound

HRID 2390062Notes

Reaction equation

HRID 2390062 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:35]=[C:36]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:37]=1)[CH2:12][NH:13][CH2:14][CH2:15][N:16]1[CH:25]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:34])[CH:22]=2)[CH2:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:53](Cl)([O:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)=[O:54].C(=O)(O)[O-].[Na+]>ClCCl.C(Cl)(Cl)Cl>[CH2:56]([O:55][C:53]([N:13]([CH2:12][C:11]1[CH:35]=[C:36]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:37]=[C:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH:10]=1)[CH2:14][CH2:15][N:16]1[CH:25]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)[CH2:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:34])[CH:22]=2)[CH2:17]1)=[O:54])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 59323140HCID 59323140, compound

Product 1

HCID 59323111HCID 59323111, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

31.5 mg of N-[3,5-bis(tert-butyloxycarbonyl)aminobenzyl]-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine was taken into a 20-mL eggplant flask and dissolved in 1.5 mL of dichloromethane, and 0.01 mL of triethylamine and 0.01 mL of Cbz-chloride were sequentially added thereto under ice-cooling, followed by stirring for 1 hour at room temperature. After completion of the reaction, to the reaction liquid were added a saturated aqueous sodium bicarbonate solution and chloroform under ice-cooling. The organic layer was separated, the aqueous layer was further extracted by addition of chloroform, and the organic layer was combined and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, and the solvent was removed by evaporation to obtain 120.0 mg of a crude composition. The crude composition was purified by PLC to obtain 35.8 mg (yield 93%) of a title compound as a pale yellow oily substance.

Workup

  1. temperatureunder ice-cooling
  2. customAfter completion of the reaction
  3. customto the reaction liquid
  4. temperaturecooling
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was further extracted by addition of chloroform
  7. washwashed with saturated brine
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customthe solvent was removed by evaporation
  11. customto obtain 120.0 mg of a crude composition
  12. customThe crude composition was purified by PLC

Sources & evidence

ORD record
ord-5b5cc1402b08462d9f97b063673b23a4
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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