Acetic Anhydride → HCID 23347653, compound

HRID 1855693Notes

Reaction equation

HRID 1855693 reaction equation
[NH2:1][C:2](=[C:6]([OH:10])[CH2:7][O:8][CH3:9])[C:3]([OH:5])=[O:4].[C:11](OC(=O)C)(=[O:13])[CH3:12]>O>[C:11]([NH:1][CH:2]([CH:6]([OH:10])[CH2:7][O:8][CH3:9])[C:3]([OH:5])=[O:4])(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride3×HCID 76374626HCID 76374626, compound

Product 1

HCID 23347653HCID 23347653, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of amino acid 7 (34 g, 0.23 mol) in 300 ml of water cooled to 0° was added dropwise with stirring, 10 ml of acetic anhydride. After 1 hr, an additional 10 ml of acetic anhydride was added. The process was continued until a total of 35 ml of acetic anhydride had been added. The reaction mixture was allowed to stand at 0° for 3 hrs. The solvent was then removed in vacuo at 50°. Water was added to the residue and after a homogeneous solution was obtained, the water was removed in vacuo at 50°. The addition and removal of water was repeated 3 more times. The resultant residue was subjected two more times to the entire sequence beginning with the addition of 35 ml of acetic anhydride in portions. The residue resulting from this treatment was dried in vacuo (0.1 mm) for 48 hr yielding 2-Acetamido-3-hydroxy-4-methoxybutanoic acid as a glass. This material was used directly in the next step.

Workup

  1. additionwas added dropwise
  2. additionhad been added
  3. waitto stand at 0° for 3 hrs
  4. customThe solvent was then removed in vacuo at 50°
  5. additionWater was added to the residue
  6. customafter a homogeneous solution was obtained
  7. customthe water was removed in vacuo at 50°
  8. additionThe addition and removal of water
  9. additionwith the addition of 35 ml of acetic anhydride in portions
  10. customThe residue resulting from this treatment
  11. customwas dried in vacuo (0.1 mm) for 48 hr

Sources & evidence

ORD record
ord-ce03e59939124c4f9c7e6dae599ea375
Source dataset
uspto-grants-1980_08
Patent number
US04216008

Reaction notes

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