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Tetrahydrofuran → HCID 58531339, compound

HRID 1889725
Notes
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Reaction equation

HRID 1889725 reaction equation
[Cl:1][C:2]1[C:3]([OH:32])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[N:27]=[C:26]([C:28]([O:30]C)=[O:29])[CH:25]=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[C:3]([OH:32])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[N:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58531362Methyl 6-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)-methyl)picolinate

Product 1

HCID 58531339HCID 58531339, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 6-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)picolinate (0.185 g, 0.37 mmol), 1 N NaOH (2 mL), THF (2 mL) and MeOH (2 mL) was stirred at rt overnight. The reaction mixture was concentrated in vacuo and the residue was diluted with ethyl acetate and 1 N HCl. The organic layer was separated, washed with brine, dried over MgSO4, filtered and the filtrate solution was concentrated to give the desired product (0.18 g, 99%) as a colorless oil. 1H NMR (CDCl3) δ 8.12 (d, J=8.0 Hz, 1H), 7.88 (t, J=8.0 Hz, 1H), 7.58 (d, J=4.0 Hz, 1H), 7.55 (d, J=4.0 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.06-7.03 (m, 2H), 6.93 (t, J=8.0 Hz, 2H), 4.64 (s, 2H), 4.40 (s, 2H). MS (ESI): 485.0 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue was diluted with ethyl acetate and 1 N HCl
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate solution was concentrated

Sources & evidence

ORD record
ord-9b970ddee3c148a9aa81a908ee7d08cf
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08501992B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes