Acetic Anhydride → Acetyl aspartic acid, D-

HRID 1920605Notes

Reaction equation

HRID 1920605 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@H:9]([C:21]([OH:23])=[O:22])[CH2:10][C:11](=[O:20])[O:12]CC1C=CC=CC=1.CC#N.O.CCN(CC)CC>C(#N)C>[C:1]([NH:8][C@@H:9]([C:21]([OH:23])=[O:22])[CH2:10][C:11]([OH:12])=[O:20])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 6951056HCID 6951056, compoundHCID 22261089HCID 22261089, compound

Product 1

HCID 774916Acetyl aspartic acid, D-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of acetic anhydride (85 μl, 0.90 mmol.) in acetonitrile (1 ml), there is added a solution of commercially available H-D-Asp(OBn)-OH (Senn Chemicals, CH-Dielsdorf) (200 mg, 0.90 mmol.) in a CH3CN.H2O/Et3N (3.5/1.0/0.4 ml) mixture. The reaction mixture is stirred for 18 hours at room temperature. The organic solvent is evaporated and the remaining aqueous phase is cooled down to 0° C., acidified with a 10% aqueous solution of citric acid till pH=3 and extracted with EtOAc (2×). The organic layers are pooled and dried over MgSO4, filtered and evaporated. The -benzyl ester of N-acetyl-D-aspartic acid obtained as a white crystalline solid (192 mg, 81%) is used in the next step with no further purification. (Rf=0.45 in 20/1 CH2Cl2/MeOH containing 2% of acetic acid, phosphomolybdinium compound and U.V. color development agent).

Workup

  1. customThe organic solvent is evaporated
  2. temperaturethe remaining aqueous phase is cooled down to 0° C.
  3. extractionextracted with EtOAc (2×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1f8e2f1b7f9f4a5587e707a07fc20a10
Source dataset
uspto-grants-2012_05
Patent number
US08173133B2

Reaction notes

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