HCID 178457346, compound → HCID 178457345, compound

HRID 505295Notes

Reaction equation

HRID 505295 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[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([CH2:42][C:43](O)=[O:44])[CH2:38][CH2:37]3)[CH2:32][CH2:33][CH3:34])[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>C1COCC1>[F:48][C:2]([F:1])([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[CH:25]=[C:24]([O:26][C:27]([F:28])([F:29])[F:30])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:35][C@H:36]3[CH2:37][CH2:38][C@H:39]([CH2:42][CH2:43][OH:44])[CH2:40][CH2:41]3)[CH2:32][CH2:33][CH3:34])[C@H:14]2[CH3:46])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

3

Reactant 1

HCID 178457346HCID 178457346, compound

Product 1

HCID 178457345HCID 178457345, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (trans-4-{[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](propyl)amino]methyl}cyclohexyl)acetic acid (8.8 mg, 0.0126 mmol) in THF (1 mL) was added a 1 M solution of BH3 in THF (75 μL, 0.075 mmol). The reaction was stirred at room temperature for 2 hours and then quenched with water (5 mL), diluted with EtOAc (15 mL), and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (10 to 50% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-[{[trans-4-(2-hydroxyethyl)cyclohexyl]methyl}(propyl)amino]-5-(trifluoromethoxy)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.09 (25% EtOAc/hexanes). LCMS=685.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.89 (s, 1H), 7.78 (s, 2H), 7.16 (d, J=8.9 Hz, 2H), 7.10 (d, J=8.8 Hz, 1H), 5.74 (d, J=8.0 Hz, 1H), 4.72 (d, J=16.4 Hz, 1H), 4.58 (d, J=16.4 Hz, 1H), 4.02-3.98 (m, 1H), 3.66-3.64 (m, 2H), 2.77-2.73 (m, 4H), 1.77-0.81 (m, 17H), 0.64 (d, J=6.6 Hz, 3H).

Workup

  1. customquenched with water (5 mL)
  2. additiondiluted with EtOAc (15 mL)
  3. washwashed with brine (5 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (10 to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0d404c07cc0d48f7b7caab6c325b79ab
Source dataset
uspto-grants-2010_08
Patent number
US07781426B2

Reaction notes

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