Hydrochloric Acid → 2-[4-(Methanesulfonylamino-methyl)-phenyl]-pent-4-enoic acid

HRID 23580Notes

Reaction equation

HRID 23580 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:10][CH:9]=1)[CH2:5][CH:6]=[CH2:7].O1CCCC1.O.[OH-].[Li+].Cl>O.CO>[CH3:19][S:16]([NH:15][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH:4]([CH2:5][CH:6]=[CH2:7])[C:3]([OH:20])=[O:2])=[CH:9][CH:10]=1)(=[O:18])=[O:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69731788HCID 69731788, compound

Product 1

HCID 225731892-[4-(Methanesulfonylamino-methyl)-phenyl]-pent-4-enoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 2-[4-(methanesulfonylamino-methyl)-phenyl]-pent-4-enoic acid methyl ester (1.85 g, 6.55 mmol) in a 1:1 mixture of tetrahydrofuran (25 cm3) and methanol (25 cm3) at ambient temperature under an atmosphere of dry nitrogen was added lithium hydroxide hydrate (1.16 g, 26.2 mmol) dissolved in water (25 cm3). The mixture was stirred at ambient temperature for 16 hours and volatile fractions removed in vacuo to leave an aqueous mixture. The mixture was diluted with water (25 cm3) and acidified with 1 N hydrochloric acid to pH 1.0. The aqueous mixture was extracted with dichloromethane (3×30 cm3), The combined dichloromethane extracts washed with brine (1×30 cm3), dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to a colorless oil (1.68 g, 90.7%) with a negative ion ESI (M−H)−282.1.

Workup

  1. customvolatile fractions removed in vacuo
  2. customto leave an aqueous mixture
  3. extractionThe aqueous mixture was extracted with dichloromethane (3×30 cm3)
  4. washThe combined dichloromethane extracts washed with brine (1×30 cm3)
  5. dry with materialdried over sodium sulfate, vacuum
  6. filtrationfiltered
  7. customthe filtrate volatile fractions removed in vacuo to a colorless oil (1.68 g, 90.7%) with a negative ion ESI (M−H)−282.1

Sources & evidence

ORD record
ord-2f3da7a5a7b94993849f857b4c09429c
Source dataset
uspto-grants-2005_02
Patent number
US06852713B2

Reaction notes

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