Ethyl Acetate → HCID 70166966, compound

HRID 1358134Notes

Reaction equation

HRID 1358134 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][C:6]=1[CH:7]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH:21]=O)[CH:14]=1)[O:8]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:38][CH2:39][O:40][C:41]([CH3:43])=[O:42]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][C:6]=1[CH:7]([C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[O:19][CH2:20]/[CH:21]=[CH:43]/[C:41]([O:40][CH2:39][CH3:38])=[O:42])[O:8]2

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 18189190HCID 18189190, compound

Product 1

HCID 70166966HCID 70166966, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of Example 94A (0.040 g, 0.089 mmol), triethylphosphono-acetate (0.030 g., 0.130 mmol) and cesium carbonate (0.109 g, 0.336 mmol) in toluene (1 mL) was stirred at 80° C. for 16 hours and then diluted with EtOAc (10 mL) and brine (25 mL). The layers were separated and the organic layer was dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by HPLC using aqueous 0.1% TFA and CH3CN to provide the titled compound (1H NMR (300 MHz, DMSO-d6) δ 9.85 (s, 1H), 8.33 (d, J=9.1 Hz, 1H), 7.26-7.22 (m, 2H), 7.13 (t, J=8 Hz, 1H), 6.92-6.80 (m, 4H), 6.73 (d, J=8 Hz, 1H), 6.65 (d, J=9 Hz, 1H), 6.19 (s, 1H), 6.08-6.02 (m, 2H), 4.75-4.73 (m, 2H), 4.13 (q, J=7 Hz, 2H), 3.88 (s, 3H), 3.00 (s, 3H), 1.22 (t, J=7 Hz, 3H); MS (ESI, −Q1MS) m/e 508 (M−H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-e0da07c19c314eb59c30db6489a10562
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

Loading…