Triethylamine → HCID 69414409, compound

HRID 1351318Notes

Reaction equation

HRID 1351318 reaction equation
[O:1]=[C:2]1[C:7]2[S:8][CH:9]=[C:10]([C:11]([OH:13])=O)[C:6]=2[CH2:5][CH2:4][CH2:3]1.[CH2:14]([N:16](CC)CC)[CH3:15].C(Cl)(=O)OCC.C(N)C.O1CCCC1>O1CCCC1>[CH2:14]([NH:16][C:11]([C:10]1[C:6]2[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:7]=2[S:8][CH:9]=1)=[O:13])[CH3:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 3860983STK279704HCID 66726184Ethylamine tetrahydrofuran

Product 1

HCID 69414409HCID 69414409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid (the compound of Preparation Example 4) (98 mg) in tetrahydrofuran (2 mL) was added 0.11 mL of triethylamine (0.11 mL) and ethyl chlorocarbonate (58 μL) on an ice bath. After stirring for 30 minutes, a solution (1 mL) of 2M ethylamine-tetrahydrofuran was further added dropwise and the solution was stirred for 20 minutes. After the solution was extracted with water, then was extracted with ethyl acetate, and washed with saturated sodium chloride water. After the organic layer was dried with anhydrous sodium sulfate, the solvent was removed by evaporation and the title compound (100 mg) was obtained as a reddish-brown solid.

Workup

  1. stirringthe solution was stirred for 20 minutes
  2. extractionAfter the solution was extracted with water
  3. extractionwas extracted with ethyl acetate
  4. washwashed with saturated sodium chloride water
  5. dry with materialAfter the organic layer was dried with anhydrous sodium sulfate
  6. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-865104e99ae140feb7848fb219aa7ee5
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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