Salicylaldehyde → HCID 9841928, compound

HRID 1603078Notes

Reaction equation

HRID 1603078 reaction equation
[CH2:1]([NH:13][C:14](=[O:18])[C@H:15]([CH3:17])[NH2:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+].[CH:21](=O)[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)[OH:24].[BH4-].[Na+]>CO>[CH2:1]([NH:13][C:14](=[O:18])[C@H:15]([CH3:17])[NH:16][CH2:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[OH:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 6998Salicylaldehyde2×HCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 15480970HCID 15480970, compound

Product 1

HCID 9841928HCID 9841928, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

L-alanine laurylamide (2.5 g) and 1 g of sodium hydroxide were dissolved in 20 ml of methanol, and 1.0 ml of salicylaldehyde and 0.1 g of sodium borohydride were added thereto in this order. After the mixture was stirred for 1 hour, 1.0 ml of salicylaldehyde and 0.1 g of sodium borohydride were added thereto again in this order. The mixture was stirred overnight at room temperature, and the insoluble matter was then separated through filtration. The filtrate was adjusted to a pH of 7 with hydrochloric acid, and concentrated under reduced pressure. The resulting oil was dissolved in diethyl ether, washed with water, and then dried over with magnesium sulfate. After the drying agent was separated through filtration, the filtrate was concentrated under reduced pressure to give 3 g of N-(2-hydroxybenzyl)-L-alanine laurylamide.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. customthe insoluble matter was then separated through filtration
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting oil was dissolved in diethyl ether
  5. washwashed with water
  6. dry with materialdried over with magnesium sulfate
  7. customAfter the drying agent was separated through filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7729b823018c47ff9114913af103bdfc
Source dataset
uspto-grants-1999_11
Patent number
US05985922

Reaction notes

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