Hydrochloric Acid → HCID 22804691, compound

HRID 2419842Notes

Reaction equation

HRID 2419842 reaction equation
[NH2:1][CH2:2][C@@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[C:11](=O)([O-])[O-:12].[Na+].[Na+].Cl>O.CC(C)=O>[OH:6][CH:5]([C@H:3]1[O:4][C:11](=[O:12])[NH:1][CH2:2]1)[CH:7]([OH:8])[CH2:9][OH:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 12442746HCID 12442746, compound

Product 1

HCID 22804691HCID 22804691, compoundYield 28.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1-Amino-1-deoxy-D-ribitol (2.1 g, 0.014 mole prepared from D-ribose as described by Wolfron et. al. J. Org. Chemi. 23, 571 [1958]) was dissolved in water (30 ml), and sodium carbonate (2.9 g, 28 mole) and a solution of p-nitrophenyl-chloroformate (3.2 g, 0.016 mole) in acetone (10 ml) were added at 0° C. The solution was stirred and allowed to stand at room temperature overnight. The solution was acidified with 5N hydrochloric acid and extracted several times with ethyl acetate. The aqueous phase was evaporated and the residue extracted with ethanol. Chromatography on silica eluting with a gradient of chloroform and ethanol gave 5-(S)-(1',2',3'-trihydroxypropyl)-1,3-oxazolidin-2-one (0.7 g) an an oil.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customThe aqueous phase was evaporated
  3. extractionthe residue extracted with ethanol

Sources & evidence

ORD record
ord-3ef128378f0c4c80b1f3b7f3208a007b
Source dataset
uspto-grants-1978_08
Patent number
US04107435

Reaction notes

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