Sodium Hydroxide → Bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)

HRID 976039Notes

Reaction equation

HRID 976039 reaction equation
C[C:2]([CH2:32][C:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1)([CH2:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)=[O:4].[OH-].[Na+]>CO.O1CCOCC1.O>[C:33]1([CH2:32][CH:2]([CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)[C:3]([NH:5][C@@:6]([CH3:20])([C:17]([OH:19])=[O:18])[CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)=[O:4])[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86750505Methyl bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)

Product 1

HCID 9828730Bis-(1-naphthylmethyl)acetyl-(alpha-methyl-D-tryptophan)Yield 57.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4.24 g (7.6 mmol) of methyl bis-(1-naphthylmethyl)acetyl-(α-methyl-D-tryptophan) in 50 mL MeOH and 50 mL dioxane was treated with a solution of 1.0 g (25 mmol) of NaOH in 10 mL H2O and the solution left stirring at room temperature for 4 days. The solvent was removed under reduced pressure and the residue mixed with H2O and acidified to Congo red end point with dilute HCl. The crude product was collected and chromatographed on silica gel, eluting with CHCl3 : MeOH (95:5). There was obtained 2.37 g (57.8% yield) of the product as a solid foam. The structure was confirmed by NMR and mass spectroscopy.

Workup

  1. waitthe solution left
  2. customThe solvent was removed under reduced pressure
  3. additionthe residue mixed with H2O
  4. customThe crude product was collected
  5. customchromatographed on silica gel
  6. washeluting with CHCl3 : MeOH (95:5)

Sources & evidence

ORD record
ord-a01e9f7c9a974273b448aef07047e345
Source dataset
uspto-grants-1997_03
Patent number
US05610177

Reaction notes

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