Hydrochloric Acid → HCID 57503337, compound

HRID 1669772Notes

Reaction equation

HRID 1669772 reaction equation
[C:1]([C:4]1[C@@H:5]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[O:37][C:36]([CH3:39])=[CH:35][C:34]3=[O:40])[C:6]([C:12]([O:14][C@H]2CC(=O)N(CC3C=CC=CC=3)C2=O)=[O:13])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].C1CCN2C(=NCCC2)CC1.O.Cl>C(OCC)(=O)C>[C:1]([C:4]1[C@@H:5]([C:29]2[CH:30]=[CH:31][CH:32]=[C:33]3[C:38]=2[O:37][C:36]([CH3:39])=[CH:35][C:34]3=[O:40])[C:6]([C:12]([OH:14])=[O:13])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57503336HCID 57503336, compound

Product 1

HCID 57503337HCID 57503337, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

300 mg (0.555 mmol) of (3S)-1-benzyl-2,5-dioxopyrrolidin-3-yl (4R)-5-acetyl-2,6-dimethyl-4-(2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate are dissolved in 10 ml of ethyl acetate, and 295.7 mg (1.942 mmol) of DBU are added. The mixture is stirred at room temperature for 8 h. Water is then added, and the pH is adjusted to pH 4-5 with 1 N hydrochloric acid. The aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution. After drying over magnesium sulfate, the solvent is removed in vacuo. The product obtained in this way is reacted further without purification.

Workup

  1. customThe aqueous phase is separated off
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent is removed in vacuo
  6. customThe product obtained in this way
  7. customis reacted further without purification

Sources & evidence

ORD record
ord-a86ab3afa0cd4ba1b414764a3b518fcb
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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