Sulfuric Acid → HCID 20536468, compound

HRID 1389108Notes

Reaction equation

HRID 1389108 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([NH:15]C(=O)C)[CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:5].S(=O)(=O)(O)O.[C:24]([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[CH:14]=[C:13]([NH2:15])[CH:12]=[CH:11][C:3]=1[C:4]([CH2:6][CH2:7][C:8]([O:10][CH3:24])=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 517045Sodium AcetateHCID 20536509HCID 20536509, compound

Product 1

HCID 20536468HCID 20536468, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 35 g. of 3-(2-fluoro-4-acetamidobenzoyl)propionic acid, 700 ml. of methanol and 1.4 ml. of concentrated sulfuric acid is refluxed for 76 hours. The solution is cooled to 35° C. and poured onto 7 g. of anhydrous sodium acetate while stirring. The reaction mixture is stirred in an ice-bath. The solid is collected and washed with cold methanol to yield methyl 3-(2-fluoro-4-aminobenzoyl)propionate as a white solid. A mixture of this solid, 9.2 g. of hexadecyl bromide and 4.2 g. of potassium carbonate is stirred for 20 hours at 125° C. under nitrogen. The mixture is then cooled to 25° C. and 30 ml. of water is added. After stirring, the product is filtered and washed with water. Recrystallization from methanol affords methyl 3-[2-fluoro-4-(hexadecylamino)benzoyl]propionate as a white solid.

Workup

  1. additionA mixture of 35 g
  2. additionpoured onto 7 g
  3. customThe solid is collected
  4. washwashed with cold methanol

Sources & evidence

ORD record
ord-d9714003dcb84e9393c62b152f61045b
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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