Réaction #9809

ord-273ecbc82a3a49628633bb22c5aef4ba

Équation de réaction

COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1
product
COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1
methyl (S,S)-4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-(4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-((phenylmethoxy)carbonylamino)butanoylamino)butanoate
[Li+].[OH-]
lithium hydroxide
→
O=C(CC[C@H](NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1)C(=O)O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO
product
O=C(CC[C@H](NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1)C(=O)O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO
(S,S)-4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-(4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-((phenylmethoxy)carbonylamino)butanoylamino)butanoic acid

Réactifs

COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1
product
COC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)[C@H](CCC(=O)NC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)CO)NC(=O)OCc1ccccc1
methyl (S,S)-4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-(4-(N-((R,S,S,S)-2,3,4,5,6-pentahydroxyhexyl)carbamoyl)-2-((phenylmethoxy)carbonylamino)butanoylamino)butanoate
[Li+].[OH-]
lithium hydroxide

Réactifs

Aucun

Solvants

C1CCOC1.CO
tetrahydrofuran methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe reaction is concentrated
  2. 2
    workup.ADDITIONdiluted with additional water
  3. 3
    Autrepurified by passage down an acidic ion exchange column

Mode opératoire

The product of step 11B is dissolved in tetrahydrofuran/methanol (1:1) and treated with excess 3N aqueous lithium hydroxide. The reaction is followed by HPLC for disappearance of starting material. The reaction is concentrated, diluted with additional water, and purified by passage down an acidic ion exchange column. The product fractions are lyophilized to afford the product as a solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07090828B2uspto-grants-2006_08