Sodium hydride → HCID 54689864, compound

HRID 1244134Notes

Reaction equation

HRID 1244134 reaction equation
[H-].[Na+].C(O[C:6]([C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]([O:23]CC)=[O:22])=[CH:15][CH:14]=2)=[C:11]([Cl:26])[S:10][C:9]=1[NH2:27])=[O:7])C>C1COCC1.[OH-].[Na+].CO>[Cl:26][C:11]1[S:10][C:9]2[NH:27][C:6](=[O:7])[C:8]([C:9]#[N:27])=[C:6]([OH:7])[C:8]=2[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 69607350HCID 69607350, compound

Product 1

HCID 54689864HCID 54689864, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To an ambient suspension of NaH (235 mg, 5.89 mmol, 60% dispersion in mineral oil, washed with dry hexane) in dry THF (6 mL) was added 2-amino-4-(4-ethoxycarbonylmethoxy-phenyl)-5-chloro-thiophene-3-carboxylic acid ethyl ester (1.06 g, 2.36 mmol) as a solution in THF (6 mL). The reaction was stirred overnight at room temperature and was then diluted with 1N NaOH (10 mL) and MeOH (10 mL). After stirring an additional 1.5 h at room temperature, the reaction was concentrated under reduced pressure to ˜20 mL. The solution was acidified to pH ˜1 with 1N HCl and extracted with EtOAc (3×30 mL). The combined organic layers were dried with anhydrous Na2SO4, filtered, and concentrated under reduced pressure to a beije solid that was used without further purification. MS (ESI) m/e 375 (M−H)−; 1H NMR (300 MHz, BENZENE-d6) δ ppm 4.72 (s, 2H), 6.94 (d, J=8.48 Hz, 2H), 7.26 (d, J=8.48 Hz, 2H).

Workup

  1. stirringAfter stirring an additional 1.5 h at room temperature
  2. concentrationthe reaction was concentrated under reduced pressure to ˜20 mL
  3. extractionextracted with EtOAc (3×30 mL)
  4. dry with materialThe combined organic layers were dried with anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a beije solid that
  7. customwas used without further purification

Sources & evidence

ORD record
ord-d0517dc1583944288c86c9819d5359e9
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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