Acetic Acid → HCID 19799308, compound

HRID 2081368Notes

Reaction equation

HRID 2081368 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][C:10]([CH3:13])([CH3:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7](C#CC3C=CC(CO)=CN=3)[CH:8]=2)[O:3]1.[C:25]([OH:28])(=[O:27])[CH3:26].[CH:29]1([N:35]=[C:36]=NC2CCCCC2)[CH2:34][CH2:33][CH2:32][CH2:31]C1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][C:2]1([CH3:24])[CH2:11][C:10]([CH3:12])([CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:29]3[CH:34]=[CH:33][C:32]([CH2:31][O:27][C:25](=[O:28])[CH3:26])=[CH:36][N:35]=3)[CH:8]=2)[O:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 15166492HCID 15166492, compound2×

Product 1

HCID 19799308HCID 19799308, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.09 g (10 mmol) of 2,2,4,4-tetramethyl-6-[2-(5-hydroxymethylpyrid-2-yl)ethynyl]chroman (Compound 50) 600 mg (10 mmol) of glacial acetic acid, 2.06 g (10 mmol) of dicyclohexylcarbodiimide and 460 mg (3.765 mmol) of 4-dimethylaminopyridine in 150 ml methylene chloride is stirred at room temperature for 48 hours. The reaction mixture is then filtered and the residue washed with 50 ml of methlene chloride. The filtrate is then concentrated in vacuo and the residue is purified by chromatography followed by recrystallization to give the title compound.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. washthe residue washed with 50 ml of methlene chloride
  3. concentrationThe filtrate is then concentrated in vacuo
  4. customthe residue is purified by chromatography
  5. customfollowed by recrystallization

Sources & evidence

ORD record
ord-34d7eaf7d20c4108ac94e62fc618bcde
Source dataset
uspto-grants-1993_02
Patent number
US05183827

Reaction notes

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