Beta-Alanine → HCID 68141809, compound

HRID 1288438Notes

Reaction equation

HRID 1288438 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].Cl[CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1.CS(C)=O.[C:23](=O)([O-:25])[O-:24].[Na+].[Na+]>O>[C:4]([OH:6])(=[O:5])/[CH:3]=[CH:2]/[C:23]([OH:25])=[O:24].[NH2:1][CH2:2][CH2:3][C:4]([O:6][CH2:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:5]

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 679Dimethyl SulfoxideHCID 68451-ChloromethylnaphthaleneHCID 10340Sodium Carbonate

Product 1

HCID 68141809HCID 68141809, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.89 g. (10 mmole) of 3-aminopropionic acid and 1.77 g. (10 mmole) of 1-chloromethylnaphthalene in 10 ml. dimethylsulfoxide is stirred at 60° C. for 7 hours. Water, 80 ml., is added to the cooled reaction mixture followed by a saturated sodium carbonate solution until a pH of 8 is obtained. The product is extracted into 50 ml. ethyl ether which is then washed with three 20 ml.. portions of water. After drying the ether extract over 12 g. anhydrous sodium sulfate and filtering directly into a solution of 1.0 g. fumaric acid in 30 ml. methanol, solvents are removed under reduced pressure (15-20 mm.) at 35°-40° C. The residue is recrystallized by dissolving in 25 ml. warm methanol and precipitating with 50 ml. ethyl acetate to give 1-naphthylmethyl 3-aminopropionate hydrogen fumarate, m.p. 160.7°-162.7° C. An analytical sample, m.p. 159.2°-161.2° C., is obtained after recrystallization from a similar methanol-ethyl acetate mixture.

Workup

  1. additionA mixture of 0.89 g
  2. addition, is added to the cooled reaction mixture
  3. customis obtained
  4. extractionThe product is extracted into 50 ml
  5. washethyl ether which is then washed with three 20 ml
  6. dry with materialAfter drying the ether
  7. extractionextract over 12 g
  8. filtrationanhydrous sodium sulfate and filtering directly into a solution of 1.0 g
  9. custommethanol, solvents are removed under reduced pressure (15-20 mm.) at 35°-40° C
  10. customThe residue is recrystallized
  11. dissolutionby dissolving in 25 ml
  12. customwarm methanol and precipitating with 50 ml

Sources & evidence

ORD record
ord-e7842ea2f46442568a02572445fd2129
Source dataset
uspto-grants-1976_10
Patent number
US03988341

Reaction notes

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