Phthalic Anhydride → HCID 1551691, compound

HRID 1907156Notes

Reaction equation

HRID 1907156 reaction equation
[NH2:1][C@H:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:14]=[C:13]1[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:15])[N:1]1[C@H:2]([CH2:6][CH2:7][S:8][CH3:9])[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 84815D-Methionine

Product 1

HCID 1551691HCID 1551691, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-2-amino-4-(methylthio)butanoic acid (50 g, 335 mmol), finely ground phthalic anhydride (49.6 g, 335 mmol) and triethlamine (4.67 ml, 33.5 mmol) in toluene (450 ml) was stirred and heated under vigorous reflux in a Dean-Stark apparatus for 2.5 h. Volatiles were evaporated and to the residue was added 600 ml water and 6 ml hydrochloric acid and the mixture stirred vigorously with a mechanical stirrer. After stirring for 30 minutes, the suspension was filtered and filtrate evaporated under vacuum to give the title compound (87.24 g=92% yield).

Workup

  1. temperatureheated
  2. temperatureunder vigorous reflux in a Dean-Stark apparatus for 2.5 h
  3. customVolatiles were evaporated and to the residue
  4. additionwas added 600 ml water and 6 ml hydrochloric acid
  5. stirringAfter stirring for 30 minutes
  6. filtrationthe suspension was filtered
  7. customfiltrate evaporated under vacuum

Sources & evidence

ORD record
ord-1520a6cd29fa4bba97013460d00873d9
Source dataset
uspto-grants-2013_12
Patent number
US08598123B2

Reaction notes

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