Acetic Anhydride → 2-acetamido-3-(4-methoxyphenyl)propanoic Acid

HRID 1763741Notes

Reaction equation

HRID 1763741 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][CH:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:5][CH:4]=1.[OH-].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>O>[C:17]([NH:9][CH:8]([C:10]([OH:12])=[O:11])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 97118O-Methyltyrosine

Product 1

HCID 33942782-acetamido-3-(4-methoxyphenyl)propanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

O-Methyl-DL-tyrosine, 114 g., is dissolved in 500 ml. of a solution of 46 g. of sodium hydroxide in water with cooling. Acetic anhydride, 80 ml., and 50% sodium hydroxide to maintain pH 9-11 are added with continued cooling. The reaction is stirred for twenty minutes at pH 11 and is then acidified to pH 1 with continued cooling. The precipitated solid is collected by filtration, washed with a small amount of water and dried to give the above named compound, mp. 144°-146° C.

Workup

  1. dissolution, is dissolved in 500 ml
  2. additionare added with continued cooling
  3. filtrationThe precipitated solid is collected by filtration
  4. washwashed with a small amount of water
  5. customdried
  6. customto give the

Sources & evidence

ORD record
ord-9eff45662f1a45cbb5052fb22d4324ab
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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