Hydrochloric Acid → HCID 10477058, compound

HRID 1596707Notes

Reaction equation

HRID 1596707 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](/[CH:6]=[C:7](/[C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])=[C:13]([CH2:15][CH:16]=[O:17])[CH:14]=1)\[CH3:8])=[O:5])[CH3:2].CC(=C)C.C1C[O:37]CC1.[O-]Cl=O.[Na+].Cl>CC(O)(C)C.O>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4](/[CH:6]=[C:7](/[C:9]1[CH:10]=[CH:11][C:12]([O:18][CH2:19][C:20]2[C:21]([F:27])=[CH:22][CH:23]=[CH:24][C:25]=2[F:26])=[C:13]([CH2:15][C:16]([OH:37])=[O:17])[CH:14]=1)\[CH3:8])=[O:5])[CH3:29]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8255IsobutyleneHCID 23668197Sodium ChloriteHCID 86757408HCID 86757408, compound

Product 1

HCID 10477058HCID 10477058, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of (E)-[5-(2-diethylcarbamoyl-1-methylvinyl)-2-(2,6-difluorobenzyloxy)-phenyl]-acetaldehyde (4.38 g, 10.92 mmol) and 2 M isobutylene in THF (36.6 mL, 73.2 mmol) in tBuOH (70 mL) is added a solution of NaClO2 (1.58 g, 17.48 mmol) and NaH2PO4.H2O (1.96 g, 14.2 mmol) in H2O (25 mL), and the mixture is stirred at room temperature for 1.5 hours. The mixture is then acidified to pH 3 with 1 N HCl, and then extracted with ether (3×150 mL). The combined organic layers are then extracted with 1 N NaOH (3×150 mL), and the combined aqueous layers are acidified to pH 3 with conc. HCl, and then extracted with EtOAc(3×10). The combined organic phase is washed with water (1×50 mL) and brine (1×50 mL), dried over MgSO4, and concentrated in vacuo. Recrystallization from MeOH/EtOAc yields (E)-[5-(2-diethylcarbamoyl-1-methyl-vinyl)-2-(2,6-difluorobenzyloxy)-phenyl]-acetic acid; m.p.=167°-168°.

Workup

  1. extractionextracted with ether (3×150 mL)
  2. extractionThe combined organic layers are then extracted with 1 N NaOH (3×150 mL)
  3. extractionextracted with EtOAc(3×10)
  4. washThe combined organic phase is washed with water (1×50 mL) and brine (1×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customRecrystallization from MeOH/EtOAc

Sources & evidence

ORD record
ord-9947ea14c3134af59704000bb1e94051
Source dataset
uspto-grants-2001_09
Patent number
US06291530B1

Reaction notes

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