Salicylaldehyde → HCID 178443158, compound

HRID 534705Notes

Reaction equation

HRID 534705 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:21][OH:22])[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:5].[OH-].[Na+].O[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>CO>[OH:29][C:28](=[N:2][C@@H:3]([CH2:21][OH:22])[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:5])[C:27]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:26]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 14798Sodium HydroxideHCID 86661533HCID 86661533, compound

Product 1

HCID 178443158HCID 178443158, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

General procedure for synthesis of hydroxy-substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide (Compounds II-19, II-20, and II-21): A mixture of 0.40 g (1.00 mmol) of (S)-2-amino-3-hydroxy-N-tetradecylpropanamide hydrochloride, 0.04 g (1.00 mmol) of NaOH, 1.00 mmol of hydroxybenzaldehyde, and 40 mL of methanol was stirred at room temperature for eight hours. The solvent was then evaporated under reduced pressure, and the residue was washed with cooled methanol to yield (S)-2-(hydroxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide as powder.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. washthe residue was washed with cooled methanol

Sources & evidence

ORD record
ord-c87fcb7efa1342fd8a69f37d98afabcf
Source dataset
uspto-grants-2014_10
Patent number
US08853452B2

Reaction notes

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