Lithium Hydroxide → HCID 59463103, compound

HRID 1712937Notes

Reaction equation

HRID 1712937 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:20][C:19]([C:21]([O:23]CC)=[O:22])=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O.C(#N)C.CCOC(C)=O.OS([O-])(=O)=O.[K+]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[S:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 3939Lithium HydroxideHCID 59463267Ethyl 5-[2-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]phenyl]-2-thiophenecarboxylate

Product 1

HCID 59463103HCID 59463103, compoundYield 90.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516920Potassium bisulfateSolvent

Procedure

A mixture of ethyl 5-(2-{[(tert-butoxycarbonyl)-amino]methyl}phenyl)thiophene-2-carboxylate (2.05 g, 5.67 mmol) and lithium hydroxide (0.679 g, 28.4 mmol) in water (20 mL) and ACN (20 mL) was allowed to stir at rt for 24 h. The reaction mixture was diluted with EtOAc and 1N KHSO4. The organic solution was removed and the aqueous mixture was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered, and concentrated. The residue was dried under vacuum to give 5-(2-{[(tert-butoxycarbonyl)amino]methyl}phenyl)thiophene-2-carboxylic acid (1.71 g, 90%) as a white solid which was used without purification. LCMS: (FA) ES-332.3.

Workup

  1. customThe organic solution was removed
  2. extractionthe aqueous mixture was extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-050e4dfb7ea944498aa9eee2506c168c
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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