Acetic Acid → HCID 15166493, compound

HRID 727880Notes

Reaction equation

HRID 727880 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:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][OH:23])=[CH:18][N:17]=3)[CH:8]=2)[O:3]1.[C:25](O)(=[O:27])[CH3:26].C1(N=C=NC2CCCCC2)CCCCC1>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:14]#[C:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][O:23][C:25](=[O:27])[CH3:26])=[CH:18][N:17]=3)[CH:8]=2)[O:3]1

Participants

6

Reactant 3

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

Product 1

HCID 15166493HCID 15166493, 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-be744fd531cc42609e4dd7100a83d262
Source dataset
uspto-grants-1991_09
Patent number
US05045551

Reaction notes

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