HCID 24970137, compound → HCID 24970219, compound

HRID 604675Notes

Reaction equation

HRID 604675 reaction equation
[F:1][C:2]([F:42])([F:41])[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]([CH2:33][C:34](O)=[O:35])[CH:29]=[CH:30][C:31]=4[F:32])=[CH:24][CH:23]=[C:22]([CH:37]4[CH2:39][CH2:38]4)[N:21]=3)[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>C1COCC1>[F:42][C:2]([F:1])([F:41])[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]([CH2:33][CH2:34][OH:35])[CH:29]=[CH:30][C:31]=4[F:32])=[CH:24][CH:23]=[C:22]([CH:37]4[CH2:39][CH2:38]4)[N:21]=3)[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

3

Reactant 1

HCID 24970137HCID 24970137, compound

Product 1

HCID 24970219HCID 24970219, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-cyclopropylpyridin-3-yl]-4-fluorophenyl}acetic acid (32.8 mg, 0.055 mmol) in THF (2 mL) was added BH3 (0.22 mL of a 1M solution in THF, 0.22 mmol). The reaction was stirred at room temperature for 1 hour and then quenched with water (2 mL). The reaction was diluted with EtOAc (35 mL) and washed with water and brine (10 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-({6-cyclopropyl-3-[2-fluoro-5-(2-hydroxyethyl)phenyl]pyridin-2-yl}methyl)-4-methyl-1,3-oxazolidin-2-one. Rf=0.44 (25% EtOAc/hexanes). LCMS=583.4 (M+H)+ 1H NMR (500 MHz, CDCl3): δ 7.85 (s, 1H), 7.69 (s, 2H), 7.48 (d, J=7.8 Hz, 1H), 7.08-7.27 (m, 4H), 5.55 (d, J=7.8 Hz, 1H), 4.93 (bs, 1H), 3.82-4.10 (m, 4H), 2.85 (t, J=5.8 Hz, 2H), 2.08 (m, 1H), 1.02-1.06 (m, 4H), 0.71 (d, J=6.7 Hz, 3H).

Workup

  1. customquenched with water (2 mL)
  2. additionThe reaction was diluted with EtOAc (35 mL)
  3. washwashed with water and brine (10 mL each)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (0 to 100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bcf9fad7d43944249232d60ee4ef19f3
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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