Hydrochloric Acid → HCID 72310126, compound

HRID 2096897Notes

Reaction equation

HRID 2096897 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH:21]([CH3:40])[C:22]([OH:39])([C:27]1[CH:28]=[CH:29][C:30]2[O:35][CH2:34][C:33](=[O:36])[N:32]([CH3:37])[C:31]=2[CH:38]=1)[C:23]([F:26])([F:25])[F:24])[O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[C:8]([C:14]([F:17])([F:16])[F:15])[CH:7]=1.CC(=CC)C.Cl([O-])=[O:47].[Na+].P([O-])(O)(O)=O.[Na+].Cl>C(O)(C)(C)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH:21]([CH3:40])[C:22]([OH:39])([C:27]1[CH:28]=[CH:29][C:30]2[O:35][CH2:34][C:33](=[O:36])[N:32]([CH3:37])[C:31]=2[CH:38]=1)[C:23]([F:24])([F:26])[F:25])[O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]([OH:47])=[O:11])=[C:8]([C:14]([F:16])([F:17])[F:15])[CH:7]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86645884HCID 86645884, compound

Product 1

HCID 72310126HCID 72310126, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 4-{3-Chloro-4-[3,3,3-trifluoro-2-hydroxy-1-methyl-2-(4-methyl-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-propyl]-phenoxy}-2-trifluoromethyl-benzaldehyde (87 mg, 0.15 mmol) in tert-butanol (0.8 ml) were added 2-methyl-2-butene (52 mg, 0.74 mmol) and a solution of sodium chlorite (17 mg, 0.19 mmol) and sodium dihydrogen phosphate dehydrate (27 mg, 0.19 mmol) in water (0.6 ml) at 2° C. The mixture was stirred for 5 min. at 2° C., 17 h at r.t. and 1.5 h at 40° C. Ice water was added and the mixture was acidified using 1 M aqueous HCl. The mixture was extracted twice with AcOEt. The organic layers were washed with brine, dried (MgSO4) and concentrated. The product was purified by column chromatography (silica gel, dichhloromethane/methanol 9:1) to give the title compound (67 mg) as a white solid. MS (m/e, ISP neg. ion)=602.3 [M−H+].

Workup

  1. customat 2° C
  2. extractionThe mixture was extracted twice with AcOEt
  3. washThe organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography (silica gel, dichhloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-b1a2dcda232d49bd95d111ac75daba14
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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