Hydrochloric Acid → HCID 178494574, compound

HRID 1900061Notes

Reaction equation

HRID 1900061 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.Cl[CH:24]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl>C(N(C(C)C)C(C)C)C>[CH:24]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH2:18][CH:17]([CH2:19][O:20][CH3:21])[O:16][C:15]3=[O:22])=[CH:12][CH:13]=2)[CH2:4][CH2:3]1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7035ChlorodiphenylmethaneHCID 178494572HCID 178494572, compound

Product 1

HCID 178494574HCID 178494574, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

0.5 g of (RS)-3-[4-(trans-4-hydroxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one in 5 ml of ethyldiisopropylamine was heated with 0.35 ml of chlorodiphenylmethane to 100° and stirred at this temperature for 7 hours. The reaction mixture was cooled, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed neutral with water, dried with magnesium sulfate and concentrated. The residue (0.7 g) was chromatographed on a 30-fold amount of silica gel with methylene chloride/ethyl acetate mixtures. 0.3 g of (RS)-3-[4-(trans-4-benzhydryloxy-cyclohexyl)-phenyl]-5-methoxymethyl-oxazolidin-2-one was obtained as colorless crystals. M.p.: 146°-148°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed neutral with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue (0.7 g) was chromatographed on a 30-fold amount of silica gel with methylene chloride/ethyl acetate mixtures

Sources & evidence

ORD record
ord-796d3578c5a3405682388bd5af1787c8
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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