Triethylamine → HCID 69919635, compound

HRID 2307455Notes

Reaction equation

HRID 2307455 reaction equation
[C:1]1([CH:7]=[CH:8][C:9]([NH:11][C@H:12]([C:14]2[CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:18][CH:19]=2)[CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:28]12[CH2:34][CH:31]([NH:32][CH2:33]1)[CH2:30][O:29]2.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH:28]12[CH2:34][CH:31]([N:32]([C:16]3[CH:15]=[C:14]([C@@H:12]([NH:11][C:9](=[O:10])[CH:8]=[CH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH3:13])[CH:19]=[CH:18][CH:17]=3)[CH2:33]1)[CH2:30][O:29]2

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 36145512-Oxa-5-azabicyclo(2.2.1)heptaneHCID 86589154HCID 86589154, compound

Product 1

HCID 69919635HCID 69919635, compoundYield 16.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

Mixture of (S)-trifluoro-methanesulfonic acid 3-[1-(3-phenyl-acryloylamino)ethyl]phenyl ester (Step C in Example 82) (100 mg, 0.25 mmol), 2-oxa-5-aza-bicyclo[2.2.1]heptane (68 mg, 2eq), tetrakis (triphenylphosphine) palladium (0) (10 mol %, 29 mg), potassium carbonate (104 mg, 3eq), and triethylamine (0.2 ml) in toluene (1 ml) was stirred at 80° C. for 15 hours. Reaction mixture was diluted with 20 ml dichloromethane, washed with saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane three times. The combined organic layer was dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by flash chromatography with 40% acetone/hexane to obtain the title compound as a pale yellow solid (14 mg, 16% yield).

Workup

  1. customReaction mixture
  2. washwashed with saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane three times
  5. dry with materialThe combined organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by flash chromatography with 40% acetone/hexane

Sources & evidence

ORD record
ord-404aee4479944da9825a37cc57ebc1c2
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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