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Tetrahydrofuran → 4-Ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylic acid

HRID 453597
Notes
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Reaction equation

HRID 453597 reaction equation
[CH2:1]([N:3]1[C:10]2[CH:9]=[C:8]([C:11]([O:13]CC)=[O:12])[NH:7][C:6]=2[C:5]([N:16]([CH3:25])[S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:19])=[O:18])=[CH:4]1)[CH3:2].O1CCCC1.[OH-].[Na+]>C(O)C>[CH2:1]([N:3]1[C:10]2[CH:9]=[C:8]([C:11]([OH:13])=[O:12])[NH:7][C:6]=2[C:5]([N:16]([CH3:25])[S:17]([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:19])=[CH:4]1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59411371Ethyl 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylate

Product 1

HCID 594113874-Ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylic acidYield 85%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

To a mixture of ethyl 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylate (1.0 g), tetrahydrofuran (8 mL) and ethanol (8 mL) was added 8N aqueous sodium hydroxide solution (3 mL), and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated, 6N hydrochloric acid was added to the obtained residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was crystallized from diethyl ether to give 4-ethyl-6-[methyl(2-thienylsulfonyl)amino]-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylic acid (780 mg, yield 85%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition6N hydrochloric acid was added to the obtained residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe obtained residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-dbcd7ac17a574229bdbbcbfee6cf8bbc
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492405B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes