Methyl 4-carbamothioyl-3-methylbenzoate → methyl 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoate

HRID 607130Notes

Reaction equation

HRID 607130 reaction equation
[F:1][C:2]([F:38])([F:37])[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:30](=O)[CH:31](Br)[CH2:32][CH3:33])[C@H:14]2[CH3:36])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[NH2:39][C:40]([C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][C:43]=1[CH3:52])=[S:41]>CCO>[F:38][C:2]([F:1])([F:37])[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:27])([F:28])[F:29])[CH:23]=[CH:22][C:21]=3[C:30]3[N:39]=[C:40]([C:42]4[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][C:43]=4[CH3:52])[S:41][C:31]=3[CH2:32][CH3:33])[C@H:14]2[CH3:36])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 53832239Methyl 4-carbamothioyl-3-methylbenzoateHCID 57704842(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-bromobutanoyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one

Product 1

HCID 25010233methyl 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(2-bromobutanoyl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (25 mg, 0.040 mmol) and methyl 4-(aminocarbonothioyl)-3-methylbenzoate (16.87 mg, 0.081 mmol) in EtOH (450 μL) was heated at 70° C. overnight. The reaction was concentrated in vacuo and the residue was purified by preparative TLC (Si, 1000 microns, Hex/EtOAc (80:20)) to afford methyl 4-{4-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-5-ethyl-1,3-thiazol-2-yl}-3-methylbenzoate, as colorless oil. LCMS calc.=731.2; found=731.0 (M+1)+. 1H NMR (500 MHz, CDCl3) δ 7.99 (s, 1H); 7.92 (d, J=8.1 Hz, 1H); 7.86 (d, J=8.0 Hz, 2H); 7.79 (s, 1H); 7.72 (d, J=7.9 Hz, 1H); 7.69 (s, 1H); 7.55 (d, J=7.9 Hz, 1H); 7.29 (s, 1H); 5.59 (d, J=8.0 Hz, 1H); 4.91 (d, J=15.7 Hz, 1H); 4.27 (d, J=15.7 Hz, 1H); 4.04-3.99 (m, 1H); 3.95 (s, 3H); 2.88-2.76 (m, 2H); 2.68 (s, 3H); 1.36 (t, J=7.5 Hz, 3H); 0.57 (d, J=6.5 Hz, 3H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was purified by preparative TLC (Si, 1000 microns, Hex/EtOAc (80:20))

Sources & evidence

ORD record
ord-be06d2a161014be6b1406d7c81f70a7b
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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