Boron tribromide → 5-Chloro-N-({(5S)-3-[4-(3-hydroxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

HRID 391757Notes

Reaction equation

HRID 391757 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30]C)[C:25]4=[O:32])=[C:19]([CH3:33])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[C:21]([CH3:23])[C:20]([N:24]4[CH:29]=[CH:28][CH:27]=[C:26]([OH:30])[C:25]4=[O:32])=[C:19]([CH3:33])[CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 251670635-Chloro-N-({(5S)-3-[4-(3-methoxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Product 1

HCID 594101745-Chloro-N-({(5S)-3-[4-(3-hydroxy-2-oxopyridin-1(2H)-yl)-3,5-dimethylphenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

830 mg (1.70 mmol) of the compound from Example 71A are dissolved in 50 ml of anhydrous dichloromethane and cooled to −78° C. At this temperature, 3.40 ml (3.40 mmol) of a 1 normal boron tribromide solution in dichloromethane are added dropwise such that the temperature does not exceed −65° C. The mixture is stirred at −78° C. for 2 h and then at RT for 2.5 h and kept at −20° C. for 15 h. At room temperature, the solution is carefully added to a saturated aqueous sodium bicarbonate solution. After phase separation, the aqueous phase is extracted three times with dichloromethane, and the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated to dryness under reduced pressure. This gives 907 mg (69% of theory, purity according to LC-MS 61%) of the desired compound.

Workup

  1. customdoes not exceed −65° C
  2. waitat RT for 2.5 h
  3. waitkept at −20° C. for 15 h
  4. customAfter phase separation
  5. extractionthe aqueous phase is extracted three times with dichloromethane
  6. washthe combined organic phases are washed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3663aa18d5f44e4b92d60139b0a98959
Source dataset
uspto-grants-2013_02
Patent number
US08383822B2

Reaction notes

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