Sodium Bicarbonate → HCID 58065495, compound

HRID 909552Notes

Reaction equation

HRID 909552 reaction equation
[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:13]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C@@H:31]([CH3:34])[CH2:32][N:33]=5)=[CH:26][CH:25]=4)[CH:15]=[C:16]([O:18][C@@H:19]([CH3:23])[CH2:20][O:21]C)[CH:17]=3)=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.ClCCl.C(=O)([O-])O.[Na+]>ClCCl>[N:1]1([C:5]([C:7]2[CH:36]=[CH:35][C:10]([O:11][C:12]3[CH:17]=[C:16]([CH:15]=[C:14]([C:24]4[NH:28][C:27]([C:29]5[O:30][C@@H:31]([CH3:34])[CH2:32][N:33]=5)=[CH:26][CH:25]=4)[CH:13]=3)[O:18][C@@H:19]([CH3:23])[CH2:20][OH:21])=[C:9]([F:37])[CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22277759Boron tribromide dichloromethaneHCID 58065444HCID 58065444, compound

Product 1

HCID 58065495HCID 58065495, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5S)-2-(5-{3-[4-(Azetidin-1-ylcarbonyl)-2-fluorophenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]phenyl}-1H-pyrrol-2-yl)-5-methyl-4,5-dihydro-1,3-oxazole (337.8 mg, 0.666 mmol) synthesized in Example (69b) was dissolved in dichloromethane (10 mL), and a boron tribromide/dichloromethane solution (1M, 1 mL, 1 mmol) was added at −78° C. under nitrogen atmosphere, followed by stirring at room temperature for 1 hour. To the reaction solution, a saturated aqueous sodium hydrogencarbonate solution was added, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%) to afford the desired compound (93.7 mg, yield 29%) as a pale yellow solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: methanol/dichloromethane=2%-8%)

Sources & evidence

ORD record
ord-5ac362772ee646c1b5225e8039ae7c4c
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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