DL-alanine → HCID 77975707, compound

HRID 2164563Notes

Reaction equation

HRID 2164563 reaction equation
[C:1]([N:4]([C:10](=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])[CH:5]([C:7]([OH:9])=O)[CH3:6])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:32][CH:33]([C:35]([OH:37])=[O:36])[CH3:34]>O1CCCC1.[OH-].[Na+]>[C:1]([N:4]([C:10](=[O:18])[C:11]1[C:12](=[CH:14][CH:15]=[CH:16][CH:17]=1)[OH:13])[CH:5]([C:7]([NH:32][CH:33]([C:35]([OH:37])=[O:36])[CH3:34])=[O:9])[CH3:6])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 602DL-alanineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 77975637HCID 77975637, compound

Product 1

HCID 77975707HCID 77975707, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Acetylsalicyloyl-(DL)-alanine (2.5 g) was dissolved in dry tetrahydrofuran (15.0 ml) and dry triethylamine (1.36 ml) was added. The reaction mixture was brought to -5° C. and ethyl chloroformate (0.96 ml) was added dropwise over a period of 10 min. (DL)-Alanine (0.89 g) dissolved in aqueous sodium hydroxide (1M, 10.0 ml) was added. The reaction was allowed to proceed at 0° C. for 6 hrs., and the solvent was then removed at 30° C. under reduced pressure. The residual solution was acidified to pH 2-3 using aqueous hydrochloric acid (3M). The whole was extracted with ethyl acetate (50.0 ml), and the extract was dried (anhydrous sodium sulphate). The bulk of the ethyl acetate was removed under reduced pressure to leave a small volume of solution.

Workup

  1. customwas brought to -5° C.
  2. additionwas added
  3. custom, and the solvent was then removed at 30° C. under reduced pressure
  4. extractionThe whole was extracted with ethyl acetate (50.0 ml)
  5. dry with materialthe extract was dried (anhydrous sodium sulphate)
  6. customThe bulk of the ethyl acetate was removed under reduced pressure
  7. customto leave a small volume of solution

Sources & evidence

ORD record
ord-ec8008142ef043539bac54fd48e1e6d2
Source dataset
uspto-grants-1985_03
Patent number
US04505898

Reaction notes

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