Hydrochloric Acid → HCID 22804692, compound

HRID 2419845Notes

Reaction equation

HRID 2419845 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].ClC([O:10][C:11]1[CH:16]=C[C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)=O.Cl.[OH2:21]>CC(C)=O>[OH:10][CH:11]([C@H:12]1[O:2][C:1](=[O:4])[NH:17][CH2:14][CH2:13]1)[CH2:16][OH:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 22804692HCID 22804692, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

The product from (A), (1 g.), was dissolved in water (20 ml.) and sodium carbonate (2 g.) and a solution of p-nitrophenyl chloroformate (3 g.) in acetone (10 ml.) were added with stirring at 0° C. The solution was kept at 3° C. for 16 hours, then acidified with 5N hydrochloric acid and washed several times with ethyl acetate. The aqueous solution was evaporated and the residue was extracted with ethanol and chromatographed on a column of silica eluting with a gradient of chloroform/ethanol to give 6-(S)-(1',2'-dihydroxyethyl)tetrahydro-1,3-oxazin-2-one (0.65 g., 55%).

Workup

  1. washwashed several times with ethyl acetate
  2. customThe aqueous solution was evaporated
  3. extractionthe residue was extracted with ethanol
  4. customchromatographed on a column of silica eluting with a gradient of chloroform/ethanol

Sources & evidence

ORD record
ord-698c8a9eaa24470b8f9ebf1561e823cf
Source dataset
uspto-grants-1978_08
Patent number
US04107435

Reaction notes

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