Ethyl Acetate → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-{[3'-pyrrolidin-1-yl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one

HRID 607083Notes

Reaction equation

HRID 607083 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3I)[C@H:14]2[CH3:31])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N:34]1([C:39]2[CH:40]=[C:41](B(O)O)[CH:42]=[CH:43][CH:44]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>O.CCO.C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:41]3[CH:42]=[CH:43][CH:44]=[C:39]([N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)[CH:40]=3)[C@H:14]2[CH3:31])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 41926693-(Pyrrolidino)phenylboronic acidHCID 53363742(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 57704762(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-{[3'-pyrrolidin-1-yl-4-(trifluoromethyl)biphenyl-2-yl]methyl}-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8058HexaneSolventHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)-benzyl]-4-methyl-1,3-oxazolidin-2-one (0.05 g, 0.084 mmol), 3-(pyrrolidino)phenyl boronic acid (0.032 g, 0.167 mmol), tetrakis(triphenylphosphine) palladium (5% mol) and sodium carbonate (0.019 g, 0.18 mmol) in 7 ml of water/EtOH/toluene (1:2:4) was heated to reflux for 4 h. TLC (EtOAc:hexane/1:1) showed that the reaction was over. The solvents were removed. Water (10 ml) was added. The organic was extracted with methylene chloride (3×10 ml). The combined methylene chloride layers were washed with brine, and dried over sodium sulfate. The title compound was obtained after flash column using EtOAc:hexane/6:4 as the eluant. LC-MS (M+1): 617.0.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. customThe solvents were removed
  4. additionWater (10 ml) was added
  5. extractionThe organic was extracted with methylene chloride (3×10 ml)
  6. washThe combined methylene chloride layers were washed with brine
  7. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-dbdf427ad78941f8ac2be049ab84f217
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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