Trichloro[(methylsulfanyl)methane]boron → (S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

HRID 1675245Notes

Reaction equation

HRID 1675245 reaction equation
[B-](Cl)(Cl)(Cl)[S+](C)C.[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:43])[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([O:35]CC2C=CC=CC=2)=[CH:31][CH:30]=1)[C:24]1[CH:28]=[CH:27][O:26][N:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:43])[CH2:22][C@@H:23]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[C:24]1[CH:28]=[CH:27][O:26][N:25]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 16211690Trichloro[(methylsulfanyl)methane]boronHCID 57801834(S)-4-Benzyl-3-((S)-3-(4-(benzyloxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

Product 1

HCID 57801829(S)-4-Benzyl-3-((S)-3-(4-hydroxyphenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron trichloride methyl sulfide complex (51 mL, 2.0 M solution in DCM) was added to 7.4 (8.2 g, 17 mmol) in DCM (100 mL) at 0° C. After addition, the ice bath was removed, and the mixture was stirred at room temperature for 7 hours. The mixture was cooled in an ice bath and quenched by adding saturated sodium bicarbonate until the mixture was neutralized. More DCM (400 mL) was added, and the organic layer was separated, washed with brine, dried, and concentrated under vacuum. The crude product (6.5 g) was dissolved in 50 mL of hot MeOH. After cooling, the crystallized product was collected by filtration and washed once with MeOH to give 7.5 (4.2 g). The filtrate was concentrated, and the solid that formed was collected and washed to give an additional 1.2 g of compound 7.5. MS ESI (pos.) m/e: 393 (M+H). 1H NMR (CDCl3) δ 8.29 (d, 1H), 7.30 (m, 3H), 7.20 (d, 2H), 7.15 (d, 2H), 6.95 (d, 2H), 6.14 (d, 1H), 4.71 (dd, 1H), 4.63 (m, 1H), 4.16 (d, 2H), 4.00 (dd, 1H), 3.54 (dd, 1H), 3.21 (dd, 1H), 2.76 (dd, 1H).

Workup

  1. additionAfter addition
  2. customthe ice bath was removed
  3. temperatureThe mixture was cooled in an ice bath
  4. customquenched
  5. additionby adding saturated sodium bicarbonate until the mixture
  6. additionMore DCM (400 mL) was added
  7. customthe organic layer was separated
  8. washwashed with brine
  9. customdried
  10. concentrationconcentrated under vacuum
  11. dissolutionThe crude product (6.5 g) was dissolved in 50 mL of hot MeOH
  12. temperatureAfter cooling
  13. filtrationthe crystallized product was collected by filtration
  14. washwashed once with MeOH

Sources & evidence

ORD record
ord-542c6c5c9e7d4e0ba9e6d18b5578b169
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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