Ammonium Hydroxide → HCID 54416226, compound

HRID 264796Notes

Reaction equation

HRID 264796 reaction equation
[C:1]([NH:4][CH:5]([C:17]([OH:19])=[O:18])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH3:16])(=[O:3])[CH3:2].[OH-].[NH4+]>O>[C:1]([NH:4][C@@H:5]([C:17]([OH:19])=[O:18])[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH3:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 22309404N-Acetyl-2-methyltryptophan

Product 1

HCID 54416226HCID 54416226, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Nα -Acetyl-2-methyl-D,L-tryptophan [Y. Yabe et al. Chem. Pharm. Bull. 27(8) 1907-1911 (1979)] 1.3 g (5 mmol), was suspended in 50 ml of water and dissolved by adding concentrated ammonium hydroxide to a pH of 7.5. 5 mg of acylase (from porcine kidney, Sigma Grade III lyophilized) was added and the mixture kept at 40° C. for 24 hours. The insoluble material was separated by filtration and the filtrate was lyophilized to dryness. The residue was dissolved in the upper phase (10 ml) of n-BuOH-AcOH-H2O (16:1:20) and chromatographed on a 3.5 × 50 cm column of Sephadex G-25 (Pharmacia, Fluka) collecting 10 ml fractions. The less polar fractions (N° 16-25) were pooled to give mainly undigested Nα -acetyl-2-methyl-D-tryptophan which, without purification, was hydrolized under N2 with a solution of 1 g KOH in 25 ml of water at 100° F. for 24 hours. Acetic acid (2 ml) and water (10 ml) were added to the hot solution and placed in the refrigerator for 12 hours. The crude resulting 2-methyl-D-tryptophan was filtered, washed and dried and recrystallized from hot water (charcoal) to yield the title compound, m.p. 244°-246°, [α]D20 +18.6, [c0.26(H2O)].

Workup

  1. dissolutiondissolved
  2. customThe insoluble material was separated by filtration
  3. dissolutionThe residue was dissolved in the upper phase (10 ml) of n-BuOH-AcOH-H2O (16:1:20)
  4. customchromatographed on a 3.5 × 50 cm column of Sephadex
  5. custom(Pharmacia, Fluka) collecting 10 ml fractions

Sources & evidence

ORD record
ord-5c7edd5cff644768809789a76addec1e
Source dataset
uspto-grants-1997_07
Patent number
US05646301

Reaction notes

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