Acetone → HCID 69314810, compound

HRID 271519Notes

Reaction equation

HRID 271519 reaction equation
CON=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]3[CH:17]=[C:16]([CH2:18][N:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)[O:15][C:14]=3[C:25]3[CH:30]=[CH:29][N:28]=[C:27]([S:31][CH3:32])[N:26]=3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.Cl.CC(C)=[O:36].C(OCC)(=O)C>O1CCOCC1>[CH3:32][S:31][C:27]1[N:26]=[C:25]([C:14]2[O:15][C:16]([CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:17][C:13]=2[C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[C:4](=[O:36])[CH2:5][CH2:6]3)[CH:30]=[CH:29][N:28]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 86760763HCID 86760763, compound

Product 1

HCID 69314810HCID 69314810, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from Step 3 (0.310 g, 0.692 mmol) and 5M HCl (3 ml) in dioxane (3 ml)/acetone (1 ml) was heated at 100° C. for 1 hour. The mixture was then cooled to room temperature and poured into ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The ethyl acetate was then dried and the solvent evaporated in vacuo and the residue chromatographed on silica gel eluting with a mixture of 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95) to furnish the title compound (0.145 g, 0.345 mmol); MS(ES+) m/e 420 [M+H]+.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. dry with materialThe ethyl acetate was then dried
  4. customthe solvent evaporated in vacuo
  5. customthe residue chromatographed on silica gel eluting with a mixture of 0.880 ammonia/methanol/dichloromethane (0.5:4.5:95)

Sources & evidence

ORD record
ord-6aeece53f98245428c2d83dd04734e68
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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