Water → HCID 57062830, compound

HRID 2120465Notes

Reaction equation

HRID 2120465 reaction equation
[C:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:27]=CC=1CC(O)=O)[CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][NH:18][C:19](=O)[CH2:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[CH:13]=[CH:14][CH:15]=1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+].C1C[O:46][CH2:45][CH2:44]1>>[OH:46][CH2:45][C:44]1[CH:27]=[C:7]([CH:6]=[CH:5][C:4]=1[CH2:1][OH:2])[CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][NH:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:25])([OH:24])[CH3:23])[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69925697HCID 69925697, compound

Product 1

HCID 57062830HCID 57062830, compound

Procedure

350 mg (0.76 mmol) of 5-{[3-(3,4-bis-carboxymethylbenzyloxy)phenyl]ethylamino}-5-oxo-2-methylpentan-2-ol are dissolved in 10 ml of anhydrous THF and then 120 mg of lithium aluminium hydride (3.1 mmol) are added in two equal portions. After heating under reflux for 4 hours, the reaction medium is cooled and then sequentially treated with 120 l of water, 120 l of a 15% NaOH solution and then 360 l of water. After stirring for 1 hour, the reaction medium is filtered, concentrated and then purified by chromatography on a silica gel. A colourless oil is obtained (m=280 mg; Y=95%).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 4 hours
  3. temperaturethe reaction medium is cooled
  4. filtrationthe reaction medium is filtered
  5. concentrationconcentrated
  6. custompurified by chromatography on a silica gel
  7. customA colourless oil is obtained (m=280 mg; Y=95%)

Sources & evidence

ORD record
ord-330ff1df702f47ce88adcb07d9e10827
Source dataset
uspto-grants-2004_02
Patent number
US06689922B1

Reaction notes

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