Acetic Acid → HCID 10831118, compound

HRID 1604292Notes

Reaction equation

HRID 1604292 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH:10]=[C:11]2[N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:3]1.O.NN.C(O)(=O)C>CCO>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 15462429HCID 15462429, compound

Product 1

HCID 10831118HCID 10831118, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Compound 6 (200 mg, 0.590 mmol), hydrazine hydrate (0.57 ml, 1.77 mmol), and acetic acid (0.35 ml) in EtOH (20 ml) was heated at 80° C. while a stream of air was passed through the solution for 6 h. The reaction mixture was concentrated to about 10 ml and after cooling, it was diluted with EtOAc (30 ml) followed by washing with saturated aqueous NaHCO3 (10 ml×2), and brine (10 ml ×2), dried (Na2SO4) and concentrated to give a crude product (190 mg). This was purified by FCC (silica gel, CH2Cl2 /EtOH, (30:1)) to give the Compound 8 (150 mg, 74.6%), mp 246-248° C. 1H NMR (300 MHz, CDCl3): δ 0.56 (3H, s, 18-Me), 1.01 (3H, s, 19-Me), 3.53 (1H, m, 3α-H), 4.19 (1H, t, J=9.6 Hz, 17α-H), 5.37 (1H, d, J=5.2 Hz, 6-H), 7.93 (1H, s, 3'-H) and 8.10 (1H, s, 5'-H). Analysis calculated for C21H31ON3 : C, 73.85; H, 9.16; N, 12.31. Found: C, 73.75; H, 9.40; N, 12.28.

Workup

  1. concentrationThe reaction mixture was concentrated to about 10 ml
  2. temperatureafter cooling
  3. additionit was diluted with EtOAc (30 ml)
  4. washby washing with saturated aqueous NaHCO3 (10 ml×2), and brine (10 ml ×2)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a crude product (190 mg)
  8. customThis was purified by FCC (silica gel, CH2Cl2 /EtOH, (30:1))

Sources & evidence

ORD record
ord-6ab36954463346fb8cebf54dcbf34846
Source dataset
uspto-grants-1999_11
Patent number
US05994335

Reaction notes

Loading…