Improved Synthesis of the Biologically Active Methionine Analog, L-2-Amino-4-methoxy-<u>cis</u>-but-3-enoic Acid (L-<u>cis</u>-amb) Using an Electrophilic Glycinate Synthon

Alks, Vitauts; Sufrin, Janice R.

doi:10.1080/00397918908051040

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Cited by 8 publications

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“…8 Efficient condensation of the derivative of 2, hemiacetal MeOCH(OH)CO 2 Me, with acetamide has been reported. 9 However, attempts to follow the similar procedure to condense 2 with acetamide in refluxing toluene did not give satisfactory conversion and yield. 10 After several experiments, we found that introducing HOAc to the reaction solution improved the reaction rate as well as the conversion significantly.…”

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A Practical Preparation of EthylN-Acyl-2-(dimethoxyphosphoryl)glycinate

Xu¹,

Devine²

2010

Org. Process Res. Dev.

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“…Readily available ethyl glyoxalate ( 2 ) became our inexpensive starting material of choice . Efficient condensation of the derivative of 2 , hemiacetal MeOCH(OH)CO 2 Me, with acetamide has been reported . However, attempts to follow the similar procedure to condense 2 with acetamide in refluxing toluene did not give satisfactory conversion and yield .…”

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confidence: 99%

A Practical Preparation of EthylN-Acyl-2-(dimethoxyphosphoryl)glycinate

Xu¹,

Devine²

2010

Org. Process Res. Dev.

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ChemInform Abstract: Improved Synthesis of the Biologically Active Methionine Analog, L‐2‐Amino‐4‐methoxy‐cis‐but‐3‐enoic Acid (L‐cis‐amb) Using an Electrophilic Glycinate Synthon.

Alks

Sufrin

1990

ChemInform

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ChemInform Abstract The methyl glyoxylate hemiacetal (I) is treated with acetamide (II) and then subjected to substitution of the hydroxy group, producing the N-acetylbromoglycinate (IV). This is coupled with Z-methoxyvinyllithium, generated from the Z/E-mixture of the bromovinyl methyl ether (VI), to give a low yield of the cis-2-(acetylamino)methoxybutenoate (VII) which is a direct precursor of the amino acid (VIII) mentioned in the title. This method has been developed in order to obtain pure (VII) in contrast to known procedures which form mixtures of (VII) and its E-isomer.

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Functions Incorporating a Halogen and Another Heteroatom Group Other Than a Chalcogen

Campbell¹,

Jaap²

1995

Comprehensive Organic Functional Group Transformations

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Improved Synthesis of the Biologically Active Methionine Analog, L-2-Amino-4-methoxy-cis-but-3-enoic Acid (L-cis-amb) Using an Electrophilic Glycinate Synthon

Cited by 8 publications

References 11 publications

A Practical Preparation of EthylN-Acyl-2-(dimethoxyphosphoryl)glycinate

A Practical Preparation of EthylN-Acyl-2-(dimethoxyphosphoryl)glycinate

ChemInform Abstract: Improved Synthesis of the Biologically Active Methionine Analog, L‐2‐Amino‐4‐methoxy‐cis‐but‐3‐enoic Acid (L‐cis‐amb) Using an Electrophilic Glycinate Synthon.

Functions Incorporating a Halogen and Another Heteroatom Group Other Than a Chalcogen

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