Sodium Chloride → HCID 19603678, compound

HRID 1604680Notes

Reaction equation

HRID 1604680 reaction equation
[Cl-].[Na+].[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[C:30]5[C:25](=[CH:26][C:27]([O:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:28][CH:29]=5)[C:24]([CH:40]=[O:41])=[CH:23]4)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].P([O-])([O-])(O)=[O:43].[Na+].[Na+].S.[Na]>C(O)(C)(C)C.O1CCCC1.O>[C:3]([C:7]1[N:8]=[C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[C:30]5[C:25](=[CH:26][C:27]([O:31][CH2:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:28][CH:29]=5)[C:24]([C:40]([OH:43])=[O:41])=[CH:23]4)=[CH:17][C:15]=3[CH:16]=2)[S:10][CH:11]=1)([CH3:4])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 24203Sodium Phosphate, DibasicHCID 19603778HCID 19603778, compoundHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 19603678HCID 19603678, compoundYield 31.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium chloride (19 mg) was added to a mixture of 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-[3-(ethoxycarbonyl)propoxy]indole-3-carbaldehyde (0.31 g), sodium hydrogenphosphate 12 water (90 mg) and 2-methyl-2-butane (0.27 ml) in a mixed solvent of water (1.5 ml), tetrahydrofuran (2.2 ml) and tert-butanol (6.5 ml). After 2 days, aqueous sodium hydrogensulfide solution was added to the mixture. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of toluene and ethyl acetate. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-[3-(ethoxycarbonyl)propoxy]indole-3-carboxylic acid (0.10 g).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with a mixture of toluene and ethyl acetate
  6. additionThe fractions containing the objective compound
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09721c8e0a1244748949a723be2df000
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…