Hydrochloric Acid → HCID 53234530, compound

HRID 1476166Notes

Reaction equation

HRID 1476166 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:18])=[C:6]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])[CH:7]=1.[C:19](OC(=O)CC)(=O)[CH2:20][CH3:21].Cl>C(N(CC)CC)C>[CH2:20]([C:21]1[O:18][C:5]2[C:6]([C:8](=[O:17])[C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31263Propionic anhydrideHCID 53234531HCID 53234531, compound

Product 1

HCID 53234530HCID 53234530, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Intermediate 66 (1.1 g, 4.43 mmoles) was taken in a RB flask and to this triethylamine (10 ml) and propionic anhydride (1.80 g, 13.86 mmoles) were added and the mixture was refluxed for 24 h. After cooling to RT, the reaction mixture was acidified by the addition of 1N HCl solution, extracted with ethyl acetate, washed with sodium bicarbonate solution, dried with sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (0.800 g, 63% yield). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 7.82(dd, J=9.0,4.4Hz, 1H), 7.75(m,2H), 7.50(m,1H), 7.37-7.28(m, 3H), 2.56(m,2H), 1.19(t, J=7.6Hz, 3H).

Workup

  1. additionwere added
  2. temperaturethe mixture was refluxed for 24 h
  3. extractionextracted with ethyl acetate
  4. washwashed with sodium bicarbonate solution
  5. dry with materialdried with sodium sulphate
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-a9b2814e0f644076aa29bf193e97a3af
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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