2-Methoxyphenylacetic acid → HCID 53666438, compound

HRID 1780968Notes

Reaction equation

HRID 1780968 reaction equation
[CH3:1][C@@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[NH:3]1.C([Li])CCC.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][C:28](O)=[O:29].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:1][C@@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:28](=[O:29])[CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][CH3:19]

Participants

8

Reactant 4

HCID 71342-Methoxyphenylacetic acidHCID 25517Ammonium ChlorideHCID 6544465HCID 6544465, compoundHCID 178418339Butyllithium

Product 1

HCID 53666438HCID 53666438, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 27.4 g of (4R,5R)-4-methyl-5-phenyl-2-oxazolidinone in 200 cm3 of dry tetrahydrofuran are added, at -78° C., 100 cm3 of a 1.6M butyllithium solution in hexane, followed by addition of 33.12 g of a solution of 2-methoxyphenylacetic acid in 30 cm3 of tetrahydrofuran. The mixture is stirred for 30 minutes at this temperature and then allowed to return to room temperature. 200 cm3 of saturated aqueous ammonium chloride solution are subsequently poured in, followed by 200 cm3 of ethyl acetate. The organic phase is washed three times with 300 cm3 of water, and then with 300 cm3 of saturated aqueous sodium chloride solution, and dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The residue is taken up in 100 cm3 of diethyl ether. 35.5 g of (4R,5R)-4-methyl-5-phenyl-3-[(2-methoxyphenyl)acetyl]-2-oxazolidinone are obtained, in the form of white crystals melting at 126° C.

Workup

  1. customto return to room temperature
  2. washThe organic phase is washed three times with 300 cm3 of water
  3. dry with materialwith 300 cm3 of saturated aqueous sodium chloride solution, and dried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-305680a96b9241db832c63f34167b873
Source dataset
uspto-grants-1997_05
Patent number
US05631279

Reaction notes

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