Hydrochloric Acid → 3-{[[4-(Benzyloxy)butyl](propyl)amino]carbonyl)-5-methylbenzoic acid

HRID 14044Notes

Reaction equation

HRID 14044 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:28][CH2:29][CH3:30])[C:14]([C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:19]([O:21]CC)=[O:20])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.C(O)C.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:28][CH2:29][CH3:30])[C:14]([C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[C:19]([OH:21])=[O:20])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21086098Ethyl 3-{[[4-(benzyloxy)butyl](propyl)amino]carbonyl}-5-methylbenzoate

Product 1

HCID 210856863-{[[4-(Benzyloxy)butyl](propyl)amino]carbonyl)-5-methylbenzoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a mixture of ethyl 3-{[[4-(benzyloxy)butyl](propyl)-amino]carbonyl}-5-methylbenzoate (1.75 g, 4.25 mmol) in THF/ethanol/water (1/2/1, 30 mL) is added lithium hydroxide (0.31 g, 12.76 mmol). The reaction mixture is stirred for 2 h and then acidified to pH=3 with concentrated hydrochloric acid (0.5 mL). The reaction mixture is extracted with ethyl acetate (2×30 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 3-{[[4-(benzyloxy)butyl](propyl)-amino]carbonyl}-5-methylbenzoic acid (IX, 1.63 g), ESI-MS (m/z) [M+H]+=384.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (2×30 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9068acf9c2d54f6d985646a97cf84582
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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