Hydrochloric Acid → HCID 54170114, compound

HRID 362752Notes

Reaction equation

HRID 362752 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5].[CH3:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15].Cl>[OH-].[Na+].C1COCC1>[CH3:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][C:4]([OH:6])=[O:5])=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 424(+-)-Aspartic AcidHCID 889692-Methoxybenzoyl chloride2×

Product 1

HCID 54170114HCID 54170114, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent3×

Procedure

10 g of DL-aspartic acid (Aldrich) are dissolved in 105 ml of a 2.5N aqueous sodium hydroxide solution (60 ml)/THF (45 ml) mixture in a 500 ml, three-necked, round-bottomed flask equipped with a phmeter and with two dropping funnels containing, on the one hand, a 2.5N aqueous sodium hydroxide solution and, on the other hand, 2-methoxybenzoyl chloride. The 2-methoxybenzoyl chloride is added dropwise while maintaining the pH above 9 by simultaneous addition of the 2.5N sodium hydroxide solution. The reaction mixture is kept stirring for 3 h after the end of the addition of the acid chloride before being acidified with a concentrated hydrochloric acid solution. The mixture is exhaustively extracted with ethyl acetate. The organic phase is washed, dried and concentrated to dryness to provide crude N-(2-methoxybenzoyl) aspartic acid. The product can be used as is in the second stage (nonoptimized yield 75%) or purified by washing with a suitable organic solvent. 1H NMR 500 MHz (d6 -DMSO, δppm): 2.83 (m, 2H, H9), 3.92 (s, 3H, H12); 4.80 (m, 1H, H8), 7.07 (d.d.d, 1H, H4), 7.18 (d.d, 1H, H2), 7.52 (d.d.d, 1H, H3), 7.91 (d.d, 1H, H5), 8.85 (d, 1H, NH), 12.68 (s, 2H, OH).

Workup

  1. customthree-necked, round-bottomed flask equipped with a phmeter and with two dropping funnels
  2. additioncontaining, on the one hand
  3. temperaturewhile maintaining the pH above 9
  4. extractionThe mixture is exhaustively extracted with ethyl acetate
  5. washThe organic phase is washed
  6. customdried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-193111ccfadb4d73accd55a5a40bc5a2
Source dataset
uspto-grants-1999_02
Patent number
US05871755

Reaction notes

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