Tetrahydrofuran → HCID 66895427, compound

HRID 19336Notes

Reaction equation

HRID 19336 reaction equation
C[O:2][C:3](=[O:23])[C@@H:4]([N:9]1[CH2:13][C:12]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])=[CH:11][C:10]1=[O:22])[CH2:5][CH2:6][S:7][CH3:8].O1CCCC1.O.[OH-].[Li+]>O>[Cl:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][C:12]1[CH2:13][N:9]([C@@H:4]([CH2:5][CH2:6][S:7][CH3:8])[C:3]([OH:23])=[O:2])[C:10](=[O:22])[CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 66894930(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester

Product 1

HCID 66895427HCID 66895427, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid methyl ester (513 mg, 1.44 mmol) in a 1:1 solution of tetrahydrofuran:water (20 mL) was treated with lithium hydroxide monohydrate (120 mg, 2.88 mmol) and stirred for 1.5 h at 25° C. After such time, the mixture was concentrated in vacuo to remove the tetrahydrofuran and partioned between 1N aqueous hydrochloric acid (10 mL) and ethyl acetate (20 mL). The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methylsulfanyl-butyric acid (438 mg, 89%) as a light amber gum.

Workup

  1. concentrationAfter such time, the mixture was concentrated in vacuo
  2. customto remove the tetrahydrofuran
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13d4f24ae7b942b1b42ec4bd38059810
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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