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Tetrahydrofuran → methyl 3'-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropenylpyridin-3-yl]-4'-methoxy-2-methylbiphenyl-4-carboxylate

HRID 604657
Notes
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Reaction equation

HRID 604657 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[CH:39]=[CH:38][C:37]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][C:35]=5[CH3:44])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22](Cl)[N:21]=3)[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:49](B(O)O)([CH3:51])=[CH2:50].C(=O)([O-])[O-].[K+].[K+].C1COCC1>[Pd](Cl)Cl.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[C-]1(P(C(C)(C)C)C(C)(C)C)C=CC=C1.[Fe+2].C(Cl)Cl>[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[C:25]([C:26]4[CH:27]=[C:28]([C:34]5[CH:39]=[CH:38][C:37]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][C:35]=5[CH3:44])[CH:29]=[CH:30][C:31]=4[O:32][CH3:33])=[CH:24][CH:23]=[C:22]([C:49]([CH3:51])=[CH2:50])[N:21]=3)[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 57576282methyl 3'-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4'-methoxy-2-methylbiphenyl-4-carboxylate

Product 1

HCID 24970054
methyl 3'-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropenylpyridin-3-yl]-4'-methoxy-2-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178454861HCID 178454861, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 3′-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate (120 mg, 0.966 mmol), isopropenylboronic acid (74.4 mg, 0.865 mmol), 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride (23.5 mg, 20%), aqueous potassium carbonate (1.21 mL, 1M, 1.21 mmol) and THF (1.2 mL) were heated in an 80° C. oil bath for 1 h and 25 min. Volatiles were then removed from the crude mixture under reduced pressure. The pot residue was treated with water followed by EtOAc extraction. The combined extracts were dried over Na2SO4 followed by filtration and concentration to afford a dark colored oil. The resulting oil was purified by a reversed-phase prep-HPLC (Kromasil 100-5C18, 100×21.1 mm) eluting with a MeCN (0.1% TPA, v/v)/H2O (0.1% TFA, v/v) gradient mixture. Related fractions were pooled and evaporated in vacuo to afford a light yellow oil. The oil was dissolved with CH2Cl2 and then washed with NaHCO3 (sat. aq.). The organic layer was separated and back washed with water, separated and dried over Na2SO4, filtered and concentrated in vacuo to afford methyl 3′-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-isopropenylpyridin-3-yl]-4′-methoxy-2-methylbiphenyl-4-carboxylate, as a light yellow glass. LCMS calc.=698.22; found 699.23 (M+1).

Workup

  1. custom25 min
  2. customVolatiles were then removed from the crude mixture under reduced pressure
  3. additionThe pot residue was treated with water
  4. extractionfollowed by EtOAc extraction
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfollowed by filtration and concentration
  7. customto afford a dark colored oil
  8. customThe resulting oil was purified by a reversed-phase prep-HPLC (Kromasil 100-5C18, 100×21.1 mm)
  9. washeluting with a MeCN (0.1% TPA, v/v)/H2O (0.1% TFA, v/v) gradient mixture
  10. customevaporated in vacuo
  11. customto afford a light yellow oil
  12. washwashed with NaHCO3 (sat. aq.)
  13. customThe organic layer was separated
  14. washback washed with water
  15. customseparated
  16. dry with materialdried over Na2SO4
  17. filtrationfiltered
  18. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fb35718bda34c36810be8cc8e648c20
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07910592B2

Reaction notes

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