Citric Acid → HCID 68310074, compound

HRID 470697Notes

Reaction equation

HRID 470697 reaction equation
[OH-:1].[Na+].ClC1C=C2C([C@@]3([C@@H](C4C=CN=C(Cl)C=4F)[C@H](C(N[C@H:29]4[CH2:34][CH2:33][C@H:32]([C:35]5[O:36][CH:37]=[N:38]N=5)[CH2:31][CH2:30]4)=O)NC43CCC(C)(C)CC4)C(=O)N2)=CC=1.C(O)(=O)C[C:49]([CH2:54][C:55](O)=O)([C:51]([OH:53])=[O:52])[OH:50].O1CC[CH2:62][CH2:61]1>>[CH2:35]([O:36][C:37]([NH:38][C@H:61]1[CH2:62][O:50][C@H:49]([C:51]([OH:53])=[O:52])[CH2:54][CH2:55]1)=[O:1])[C:32]1[CH:31]=[CH:30][CH:29]=[CH:34][CH:33]=1

Participants

5

Reactant 4

HCID 311Citric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 178423626HCID 178423626, compound

Product 1

HCID 68310074HCID 68310074, compoundYield 100%

Procedure

1N sodium hydroxide solution (55.4 ml, 55.4 mmol) was added to a tetrahydrofuran (110 ml) solution of the compound (8.12 g, 27.7 mmol) obtained in Step 2 above at room temperature and the resulting mixture was stirred for 2 hours. 10% Citric acid solution was added under ice cooling, followed by extraction with ethyl acetate. Then the organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate, then the solvent was concentrated under reduced pressure and the residue was dried under reduced pressure to give 7.78 g (100%) of the title compound as a colorless solid.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThen the organic layer was washed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-be5fbb40eed74387af4bc62d63121912
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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