Sodium Bicarbonate → HCID 22258010, compound

HRID 1611018Notes

Reaction equation

HRID 1611018 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[S:5][C:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C(=O)(O)[O-].[Na+]>CC(C)C(O)=O.O>[CH3:4][CH:8]([CH3:9])[CH2:7][NH:3][C:4]1[S:5][C:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 3792137ethyl 2-amino-5-benzylthiophene-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 22258010HCID 22258010, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6590Isobutyric AcidSolvent

Procedure

Sodium borohydride (3.0 g) was added in 6 portions over 3 hours to a stirred solution of ethyl 2-amino-5-(phenylmethyl)thiophene-3-carboxylate in 2-methylpropanoic acid under nitrogen. The mixture was stirred at room temperature for 20 hours and was then diluted with water, neutralized with sodium bicarbonate and extracted with ethyl acetate four times. The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography, eluting with diethyl ether:isohexane (1:19) to give the subtitle compound (2.80 g).

Workup

  1. extractionextracted with ethyl acetate four times
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with diethyl ether:isohexane (1:19)

Sources & evidence

ORD record
ord-6f0e3dc80e464515bcfff6f6f329ac9c
Source dataset
uspto-grants-2006_01
Patent number
US06984644B2

Reaction notes

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