Triethylamine → HCID 67315421, compound

HRID 533284Notes

Reaction equation

HRID 533284 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:31](=O)CC(OCC)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C([N:54](CC)CC)C>O1CCCC1.ClCCl.C(OCC)(=O)C.O>[C:1]1([O:11][CH2:12][CH2:13][CH2:14][N:15]2[C:23]3[C:18](=[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[CH:20]=[CH:21][CH:22]=3)[CH:17]=[C:16]2[C:31]#[N:54])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 67316730HCID 67316730, compound

Product 1

HCID 67315421HCID 67315421, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of EXAMPLE 168A (880 mg) in tetrahydrofuran (10 mL) and dichloromethane (2 ml) and triethylamine (2 ml) was added, followed by the addition of trifluoroacetic anhydride (2 ml) dropwise. After the addition, the mixture was stirred for 3 hours at 0° C. After this time the mixture was diluted with ethyl acetate (200 mL) and water (80 mL). The aqueous layer was extracted with ether twice. The combined extracts were washed with water (×3), brine and dried over Na2SO4. Evaporation of solvent gave crude product.

Workup

  1. additionwas added
  2. additionAfter the addition
  3. extractionThe aqueous layer was extracted with ether twice
  4. washThe combined extracts were washed with water (×3), brine
  5. dry with materialdried over Na2SO4
  6. customEvaporation of solvent
  7. customgave crude product

Sources & evidence

ORD record
ord-bdeeefcffdac494a9c00ae7da5ba7956
Source dataset
uspto-grants-2014_10
Patent number
US08853209B2

Reaction notes

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