Sodium Chloride → HCID 54300732, compound

HRID 1855694Notes

Reaction equation

HRID 1855694 reaction equation
[C:1]([NH:4][CH:5]([CH:9]([OH:13])[CH2:10][O:11][CH3:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].[CH3:14]OS(OC)(=O)=O.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>O.[OH-].[K+]>[CH3:14][O:7][C:6](=[O:8])[CH:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:9]([OH:13])[CH2:10][O:11][CH3:12]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6497Dimethyl SulfateHCID 516892Sodium Bicarbonate2×HCID 23347653HCID 23347653, compound

Product 1

HCID 54300732HCID 54300732, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

The crude carboxylic acid was dissolved in 250 ml of water and the solution neutralized (pH 7 as indicated by pH paper) in 1 N KOH. Dimethylsulfate (30 ml) was added and the resultant two phase system was stirred vigorously for 21/2 hrs. During this time, the pH was maintained at approximately 7 by the periodic addition of saturated sodium bicarbonate solution. The temperature was then brought to 60° for 45 min and solid sodium bicarbonate was added in order to maintain pH 7. The reaction mixture was cooled, saturated with sodium chloride, and extracted 3 times with chloroform (250 ml). The extracts were dried over anhydrous sodium sulfate and concentrated in vacuo yielding 2-acetamido-3-hydroxy-4-methoxybutanoic acid methyl ester (8) as a beige solid. Crystallization from methylene chloride/petroleum ether (bp 35°-60°) gave one of the diastereomers as a white solid: mp 131°-134.5°; IR (CHCl3) 3580, 3442, 1750, 1680, 1509, 1125 cm-1 ; NMR (CDCl3) δ6.5 (broad, 1H, NH), 4.7 (m, 1H, CHNH), 4.3 (m, 1H, CH2CH), 3.7 (s, 3H, CH3O2C--), 3.3 (singlet superimposed on a multiplet, 6H, CH3OCH2 --and HO--), 2.0 (s, 3H, CH3CONH--). (Calcd. for C8H15NO5 : C, 46.82; H, 7.37; N, 6.83. Found: C, 47.03; H, 7.48; N, 6.85).

Workup

  1. waitThe temperature was then brought to 60° for 45 min
  2. temperatureto maintain pH 7
  3. extractionextracted 3 times with chloroform (250 ml)
  4. dry with materialThe extracts were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc4932f0e21241aba540eee96dde1d02
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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