(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(4'-fluoro-5'-isopropyl-2'-methoxy-4-nitrobiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one → (4S,5R)-3-[(4-amino-4'-fluoro-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

HRID 1994628Notes

Reaction equation

HRID 1994628 reaction equation
[F:1][C:2]([F:43])([F:42])[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]([N+:26]([O-])=O)[CH:23]=[CH:22][C:21]=3[C:29]3[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:32]([F:38])=[CH:31][C:30]=3[O:39][CH3:40])[C@H:14]2[CH3:41])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO>[NH2:26][C:24]1[CH:23]=[CH:22][C:21]([C:29]2[CH:34]=[C:33]([CH:35]([CH3:36])[CH3:37])[C:32]([F:38])=[CH:31][C:30]=2[O:39][CH3:40])=[C:20]([CH2:19][N:15]2[C@@H:14]([CH3:41])[C@@H:13]([C:5]3[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:43])([F:42])[F:1])[CH:4]=3)[O:17][C:16]2=[O:18])[CH:25]=1

Participants

3

Reactant 1

HCID 11527347(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(4'-fluoro-5'-isopropyl-2'-methoxy-4-nitrobiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 11614021(4S,5R)-3-[(4-amino-4'-fluoro-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(4′-fluoro-5′-isopropyl-2′-methoxy-4-nitrobiphenyl-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (1.94 g, 3.16 mmol) in methanol (20 mL) was subject to H2 (40 psi., Parr shaker) at 20° C. for 1.5 h. LCMS indicated the presence of trace starting material. The crude mixture was filtered through a bed of Celite (521). The filtrate was evaporated in vacuo to afford a glass as the product. LC-MS: 585.32 (M+1)+. 1H NMR (CDCl3, 500 MHz) a 1:1 mixture of rotamers δ 7.83 (s, 1H), 7.67 (s, 2H), 6.93-7.06 (m, 2H), 6.87 (s, 0.5H), 6.72-6.82 (m, 1.5H), 5.57 (d, J=8.0 Hz, 0.5H), 5.36 (d, J=8.0 Hz, 0.5H), 4.77 (d, J=5.5 Hz, 0.5H), 4.74 (d, J=6.5 Hz, 0.5H), 3.95 (d, J=15.5 Hz, 0.5H), 3.75-3.86 (m, 1.5H), 3.73 (s, 3 E), 3.12-3.24 (m, 1H), 1.11-1.29 (m, 6H), 0.47 (d, J=6.5 Hz, 1.5H), 0.29 (d, J=6 Hz, 1.5H).

Workup

  1. filtrationThe crude mixture was filtered through a bed of Celite (521)
  2. customThe filtrate was evaporated in vacuo
  3. customto afford a glass as the product
  4. addition1H NMR (CDCl3, 500 MHz) a 1:1 mixture of rotamers δ 7.83 (s, 1H), 7.67 (s, 2H), 6.93-7.06 (m, 2H), 6.87 (s, 0.5H), 6.72-6.82 (m, 1.5H), 5.57 (d, J=8.0 Hz, 0.5H), 5.36 (d, J=8.0 Hz, 0.5H), 4.77 (d, J=5.5 Hz, 0.5H), 4.74 (d, J=6.5 Hz, 0.5H), 3.95 (d, J=15.5 Hz, 0.5H), 3.75-3.86 (m, 1.5H), 3.73 (s, 3 E), 3.12-3.24 (m, 1H), 1.11-1.29 (m, 6H), 0.47 (d, J=6.5 Hz, 1.5H), 0.29 (d, J=6 Hz, 1.5H)

Sources & evidence

ORD record
ord-eb3e3c6a78104241826aba8a630d26ab
Source dataset
uspto-grants-2010_01
Patent number
US07652049B2

Reaction notes

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