Methanol → HCID 19039979, compound

HRID 1684628Notes

Reaction equation

HRID 1684628 reaction equation
[F:1][C:2]([F:30])([F:29])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:25]C)[CH:21]=3)[O:16][C:15]2([CH3:28])[CH3:27])[CH:8]=1)(=[O:5])=[O:4].O.CO>Br.C(O)(=O)C.ClCCl>[F:29][C:2]([F:1])([F:30])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]2[C:23](=[O:24])[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([OH:25])[CH:21]=3)[O:16][C:15]2([CH3:27])[CH3:28])[CH:8]=1)(=[O:4])=[O:5]

Participants

7

Reactant 3

HCID 887MethanolHCID 962WaterHCID 19039955HCID 19039955, compound

Product 1

HCID 19039979HCID 19039979, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 7.0 g (0.016 mole) of the product of Example 112 in 20 mL 48% hydrobromic acid and 20 mL glacial acetic acid was refluxed for 3 hours. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was, washed with water and brine and then dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 5% methanol in dichloromethane gave 6.9 g (100% of the title product as an oil). NMR (CDCl3 : δ1.46 (d, 6H); 2.85 (m, 1H); 2.95 (m, 2H). MS (Cl, NH3) m/e: 447 (M+ +18, 100), 430 (M+ +1).

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give an oil

Sources & evidence

ORD record
ord-7b04f5df16c04bb4a8e88f12111249bb
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

Loading…