Salicylaldehyde → HCID 9841928, compound

HRID 1267260Notes

Reaction equation

HRID 1267260 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].B.[Na]>CO.C(OCC)C>[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

7

Reactant 4

HCID 6998Salicylaldehyde2×HCID 14798Sodium HydroxideHCID 15480970HCID 15480970, compoundHCID 178418435HCID 178418435, compound2×

Product 1

HCID 9841928HCID 9841928, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

L-alanine laurylamide (25 g) and 1 g of sodium hydroxide were dissolved in 20 ml of methanol. To the solution were added 1.0 ml of salicylaldehyde and 0.1 g of sodium boron hydride in this order. After the mixture was stirred for 1 hour, 1.0 ml of salicylaldehyde and 0.1 g of sodium boron hydride were added thereto again in this order. After the resulting mixture was stirred overnight at room temperature, the insoluble matter was separated through filtration, and the residue was adjusted to a pH of 7 with hydrochloric acid. The oil was obtained through concentration under reduced pressure was dissolved in diethyl ether, washed with water, and then dried over magnesium sulfate. After the drying agent was separated through filtration, the filtrate was concentrated under reduced pressure to obtain 3 g of N-(2-hydroxybenzyl)-L-alanine laurylamide.

Workup

  1. stirringAfter the resulting mixture was stirred overnight at room temperature
  2. customthe insoluble matter was separated through filtration
  3. customThe oil was obtained through concentration under reduced pressure
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customAfter the drying agent was separated through filtration
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b3da5ba041124b78a2997fbf6b54e7ac
Source dataset
uspto-grants-2003_04
Patent number
US06552061B1

Reaction notes

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