2,3-Dihydroxybutanedioic Acid → methyl (2S)-2-amino-4-(methylsulfanyl)butanoate

HRID 1283886Notes

Reaction equation

HRID 1283886 reaction equation
[NH2:1][CH:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].C(O)(=O)C(C(C(O)=O)O)O.COC1C=CC(C=O)=CC=1.O>CO>[NH2:1][C@H:2]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

6

Reactant 4

HCID 8752,3-Dihydroxybutanedioic AcidHCID 962WaterHCID 312444-MethoxybenzaldehydeHCID 351663Methionine methyl ester

Product 1

HCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateYield 111.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Similarly to Example 45 but using methyl DL-methioninate (10.033 g., 61.5 mmole) and (+)-tartaric acid (9.506 g., 63.4 mmole, 1.03 equiv.) in dried methanol (50 ml., i.e. 20% ester concentration) and adding anisaldehyde (7.5 ml., 8.43 g., 61.9 mmole, 1 equiv.) and stirring for 44 hours to give methyl L-methioninate (+)-hemitartrate (11.208 g., 58%), [α]D21 + 28.8° (c 3.038, H2O).

Sources & evidence

ORD record
ord-b7498eb9837a4043aa73ae606c77340f
Source dataset
uspto-grants-1976_08
Patent number
US03976680

Reaction notes

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