Toluene → HCID 19974141, compound

HRID 1451410Notes

Reaction equation

HRID 1451410 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:16][CH2:17][CH:18]([OH:28])[C:19]2[N:20]=[C:21]([C:24]([F:27])([F:26])[F:25])[S:22][CH:23]=2)[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>O>[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([N:16]2[CH2:17][CH:18]([C:19]3[N:20]=[C:21]([C:24]([F:26])([F:27])[F:25])[S:22][CH:23]=3)[O:28][CH:30]2[C:29]([O:33][CH3:34])=[O:32])[CH3:15])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 14347763N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Product 1

HCID 19974141HCID 19974141, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.52 g (0.0012 mol) of N-[2-(4-carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethylthiazol-4-yl)ethanamine and 0.211 g (0.0024 mol) of methyl glyoxylate and 25 ml toluene are heated at 120° C. for 10 minutes and then boiled under a water trap for 1 hour. The solution is cooled, 50 ml of ethyl acetate are added, and the mixture is shaken with 30 ml of water. The organic phase is separated off, dried over sodium sulphate and concentrated. The residue is purified on a laboratory size B prepacked column (supplied by Merck) using toluene/ethyl acetate=20:1.5 as eluant. Fraction A (diastereomer pairs A and B),

Workup

  1. customfor 1 hour
  2. temperatureThe solution is cooled
  3. customThe organic phase is separated off
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue is purified on a laboratory size B prepacked column (supplied by Merck)

Sources & evidence

ORD record
ord-ca7ad41050034fe3a4168688fde340eb
Source dataset
uspto-grants-1997_02
Patent number
US05604225

Reaction notes

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