HuagongsheHuagongshe Chemistry Print Report · For research reference only
L-Tyrosine → 4-Ethenylphenylalanine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | L-Tyrosine | HCID 6057 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | Tributylvinyltin | HCID 81998 | — |
| Reactant | (S)-Benzyl 2-amino-3-(4-hydroxyphenyl)propanoate | HCID 104541 | — |
| Reactant | Phenyl triflimide | HCID 142176 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 1,3-Dihydro-1-[(L-methionyl)-carbonylmethyl)-5-phenyl-3(R,S)-{[(N-acetyl)-phosphono-L-tyrosyl]amino}-2H-1,4-benzodiazepin-2-one | HCID 131720751 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | 4-Ethenylphenylalanine | HCID 53795738 | — |
Reaction Steps
As illustrated by FIG. 5H, tyrosine benzyl ester 111 can be converted to N-acetyltyrosine benzyl ester (2) using acetic anhydride, with the hydroxy group of the tyrosine being transformed into the trifluoromethyl sufonyl derivative 113 by using phenyl bis[(trifluoromethyl)sulfonyl]amine. Compound 113 this can be coupled to vinyltributyltin in the presence of bis(triphenylphosphine)palladium dichloride and lithium chloride to give the 4-ethenylphenylalanine derivative 114. This product, on refluxing with catechol borane and further transesterification with pinanediol, gives p-boronoethyl-2-phenylalanine derivative 116. Catalytic hydrogenation affords 117, which can be further coupled to yield the desired peptide or peptidomimetic.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05776902 |
| Source dataset | uspto-grants-1998_07 |
| ORD ID | ord-b31fff8e460e4b159eb82be68f0cac62 |
| Source note | uspto-grants-1998_07 |