Hydrochloric Acid → HCID 9870523, compound

HRID 988230Notes

Reaction equation

HRID 988230 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[C:13]([CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])[CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=O)=O.Cl>O>[C:23]([NH:22][CH2:21][CH2:20][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH:11]=[C:10]([O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]3[C:17]([CH:16]=[CH:15][CH:14]=[C:13]3[CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:19]=1)[CH:19]=[CH:18]2)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 15486877HCID 15486877, compound

Product 1

HCID 9870523HCID 9870523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 ml round-bottomed flask containing 30 ml of methanol, 0.06 g of sodium is added in small portions. When the sodium has been completely used up, 0.0033 mol of the compound obtained in Preparation 1 is added, and the mixture is stirred for 20 minutes. The methanol is removed by evaporation under reduced pressure, the residue is taken up in 15 ml of DMF, and then 0.0027 mol of the compound obtained in Step B is added. The reaction mixture is then heated at reflux for 12 hours and subsequently cooled and poured into 100 ml of water and 10 ml of 3M HCl. After extraction with ethyl acetate, the organic phase is washed with a 10% sodium hydroxide solution and then with water. After drying over MgSO4 and removal of the solvent by evaporation under reduced pressure, the title compound is obtained by recrystallisation. Beige solid.

Workup

  1. additionis added
  2. customThe methanol is removed by evaporation under reduced pressure
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for 12 hours
  5. temperaturesubsequently cooled
  6. extractionAfter extraction with ethyl acetate
  7. washthe organic phase is washed with a 10% sodium hydroxide solution
  8. dry with materialAfter drying over MgSO4 and removal of the solvent by evaporation under reduced pressure

Sources & evidence

ORD record
ord-a8337dd55e4a45a191b000b4d42d279c
Source dataset
uspto-grants-2003_10
Patent number
US06635650B2

Reaction notes

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