Acetone → HCID 135489339, compound

HRID 1636010Notes

Reaction equation

HRID 1636010 reaction equation
[CH2:1]([C:3]1[N:4]([CH:25]2[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)[N:5]=[C:6]2[C:11](=[O:12])[NH:10][C:9]([C:13]3[C:14]([O:21][CH2:22][CH2:23][CH3:24])=[N:15][CH:16]=[C:17](C#C)[CH:18]=3)=[N:8][C:7]=12)[CH3:2].S(=O)(=O)(O)O.[CH3:41][C:42](C)=[O:43]>>[C:42]([C:17]1[CH:18]=[C:13]([C:9]2[NH:10][C:11](=[O:12])[C:6]3[C:7](=[C:3]([CH2:1][CH3:2])[N:4]([CH:25]4[CH2:26][NH:27][CH2:28]4)[N:5]=3)[N:8]=2)[C:14]([O:21][CH2:22][CH2:23][CH3:24])=[N:15][CH:16]=1)(=[O:43])[CH3:41]

Participants

4

Reactant 3

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 135446054HCID 135446054, compound

Product 1

HCID 135489339HCID 135489339, compound

Procedure

The product from stage g) (1.44 g, 3.0 mmol) in acetone (50 ml) and sulphuric acid (1N, 3 ml) was treated with mercuric sulphate (268 mg, 9.0 mmol) and heated to reflux for 6 h. The reaction mixture was concentrated to ˜20 ml in vacuo, poured into sodium bicarbonate (sat. aq., 20 ml) and extracted into methylene chloride (6×20 ml). Combined organics were washed with brine (20 ml), dried over MgSO4, and concentrated to a brown oil which was taken up in 40% trifluoroacetic acid in methylene chloride (50 ml) and water (1 ml) and stirred for 1 hat room temperature. After evaporation in vacuo, the residue was purified by column chromatography (eluting with 95:5:1 methylene chloride:methanol:0.88 ammonia) to afford the title compound as a white hydroscopic foam ( 1.65 g); m.p. 128.5-130.0° C.; 1H NMR (400MHz, MeOD): δ=1.00 (t, 3H), 1.30 (t, 3H), 1.79-1.90 (m, 2H), 2.60 (s, 3H), 3.00-3.10 (q, 2H), 4.50 (t, 2H), 4.60-4.70 (m, 4H), 5.65-5.78 (m, 1H), 8.65 (s, 1 H), 8.90 (s, 1H); LRMS (TSP—positive ion) 397 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. concentrationThe reaction mixture was concentrated to ˜20 ml in vacuo
  4. additionpoured into sodium bicarbonate (sat. aq., 20 ml)
  5. extractionextracted into methylene chloride (6×20 ml)
  6. washCombined organics were washed with brine (20 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated to a brown oil which
  9. customAfter evaporation in vacuo
  10. customthe residue was purified by column chromatography (eluting with 95:5:1 methylene chloride:methanol:0.88 ammonia)

Sources & evidence

ORD record
ord-3e8b04b0dd934c1eb92839b57d096d7e
Source dataset
uspto-grants-2003_01
Patent number
US06512002B2

Reaction notes

Loading…