Hydrochloric Acid → HCID 15381153, compound

HRID 1740494Notes

Reaction equation

HRID 1740494 reaction equation
[CH3:1][O:2][CH2:3][C@@H:4]1[O:8][C:7](=[O:9])[N:6]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([C:19](OC)=[O:20])=[CH:18][C:13]=3[O:12][CH:11]=2)[CH2:5]1.Cl.O>O1CCCC1>[OH:20][CH2:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([N:6]3[CH2:5][C@H:4]([CH2:3][O:2][CH3:1])[O:8][C:7]3=[O:9])=[CH:11][O:12][C:13]=2[CH:18]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 15381152HCID 15381152, compound

Product 1

HCID 15381153HCID 15381153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

22 ml of a 2M solution (0.044 mol) of a borane-dimethyl sulphide complex in tetrahydrofuran are added, in two steps, to a solution of 3.3 g (0.011 mol) of methyl (R)-3-[5-(methoxymethyl)-2-oxooxazolidin-3-yl]benzofuran-6-carboxylate in 40 ml of tetrahydrofuran and the mixture is heated for five hours at 55° C. The mixture is hydrolysed with 1N hydrochloric acid. The mixture is poured into water and the product is extracted with dichloromethane. The organic phase is dried over sodium sulphate and concentrated under reduced pressure. The product is purified by chromatography on silica gel with a 99/1 mixture of dichloromethane and methanol. After crystallization from ethyl ether, 2.0 g of product are recovered.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe product is purified by chromatography on silica gel with a 99/1 mixture of dichloromethane and methanol
  5. customAfter crystallization from ethyl ether, 2.0 g of product
  6. customare recovered

Sources & evidence

ORD record
ord-233209f9c4654beca20ebff842656046
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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