Hydrochloric Acid → HCID 178494575, compound

HRID 1900058Notes

Reaction equation

HRID 1900058 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>C(Cl)Cl.N1C=CC=CC=1>[CH3:21][O:20][CH2:19][CH:17]1[O:16][C:15](=[O:22])[N:14]([C:11]2[CH:10]=[CH:9][C:8]([C@H:5]3[CH2:6][CH2:7][C@H:2]([O:1][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:3][CH2:4]3)=[CH:13][CH:12]=2)[CH2:18]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 178494572HCID 178494572, compound

Product 1

HCID 178494575HCID 178494575, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.5 g (1.639 mmol) of (RS)-3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one in 20 ml of methylene chloride and 5 ml of pyridine was treated dropwise with a solution of 0.95 ml (8.195 mmol) of benzoyl chloride in 10 ml of methylene chloride and stirred at room temperature for a further 3 hours. The reaction mixture was poured into ice-water, made acid with 3N hydrochloric acid and extracted with methylene chloride. The organic phase was washed with wate, dried over magnesium sulfate and the solvent was distilled off. The benzoate crystallized upon treatment with t-butyl methyl ether. There was obtained 0.52 g (77%) of benzoic acid (RS)-trans-4-[4-(5-methoxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-cyclohexyl ester. M.p.: 104°-105°.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with wate
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe benzoate crystallized upon treatment with t-butyl methyl ether

Sources & evidence

ORD record
ord-78eb0a4d99334bf3a0af235f4ac136a0
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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