2-Methyl-2-butene → 4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzoic acid

HRID 909515Notes

Reaction equation

HRID 909515 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][C:11]=1[CH3:18].CC(=CC)C.O.O.P([O-])(O)(O)=[O:41].[Na+].Cl([O-])=O.[Na+].S([O-])(O)=O.[Na+]>C(O)(C)(C)C.O>[CH3:1][O:2][CH2:3][C@H:4]([CH3:32])[O:5][C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([C:22]2[NH:23][C:24]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)=[CH:25][CH:26]=2)[CH:21]=1)[O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]([OH:41])=[O:15])=[CH:12][C:11]=1[CH3:18]

Participants

8

Reactant 5

HCID 105532-Methyl-2-buteneHCID 23665763Sodium Bisulfite2×HCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 580654454-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzaldehyde

Product 1

HCID 666816654-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzoic acidYield 113.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

4-{3-[(1S)-2-Methoxy-1-methylethoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}-3-methylbenzaldehyde (50 mg, 0.11 mmol) synthesized in Example 51 was dissolved in a mixed solvent of t-butanol (5.0 mL) and water (2.0 mL), and 2-methyl-2-butene (0.15 mL, 1.42 mmol) and sodium dihydrogen phosphate dihydrate (80 mg, 0.51 mmol) were added, followed by slow addition of sodium chlorite (25 mg, 0.28 mmol) at 0° C. and stirring at 0° C. for 2 hours under nitrogen atmosphere. An aqueous sodium hydrogen sulfite solution (5 mL) was added at 0° C., and stirring was carried out at room temperature for 10 minutes. An aqueous sodium hydrogen sulfite solution (15 mL) was added, and extraction was carried out with ethyl acetate (30 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford the desired compound (58 mg, yield ˜100%) as a yellow solid.

Workup

  1. additionwere added
  2. stirringstirring
  3. waitwas carried out at room temperature for 10 minutes
  4. extractionextraction
  5. washThe organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e241383e7529478ba54d88aa2ec9830e
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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