Pyridine → HCID 42598816, compound

HRID 875260Notes

Reaction equation

HRID 875260 reaction equation
[OH:1][C:2]1([CH2:19][OH:20])[C:6](=[O:7])[O:5][C@H:4]2[C:8]3[C@@:13]([CH3:16])([CH2:14][CH2:15][C:3]12[OH:18])[CH2:12][CH2:11][CH2:10][C:9]=3[CH3:17].[C:21](OC(=O)C)(=[O:23])[CH3:22].N1C=CC=CC=1>ClCCl.CN(C)C1C=CN=CC=1>[C:21]([O:20][CH2:19][C:2]1([OH:1])[C:6](=[O:7])[O:5][C@H:4]2[C:8]3[C@@:13]([CH3:16])([CH2:14][CH2:15][C:3]12[OH:18])[CH2:12][CH2:11][CH2:10][C:9]=3[CH3:17])(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 42598580HCID 42598580, compound

Product 1

HCID 42598816HCID 42598816, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Compound of example 2 (150 mg, 0.531 mmole) was dissolved in dichloromethane (10 mL). Acetic anhydride (54.25 mg, 0.531 mmole), pyridine (84 mg, 1.062 mmole) and 4-(dimethylamino)-pyridine (DMAP) (2 mg) were added to this solution and reaction mixture was stirred for 30 minutes. Reaction mixture was extracted with dichloromethane (3×100 mL). The dichloromethane layer was washed with water and brine and was dried over sodium sulfate. The solvent was removed and crude product was purified by crystallization using ethyl acetate/petroleum ether to obtain the title compound.

Workup

  1. customReaction mixture
  2. extractionwas extracted with dichloromethane (3×100 mL)
  3. washThe dichloromethane layer was washed with water and brine
  4. dry with materialwas dried over sodium sulfate
  5. customThe solvent was removed
  6. customcrude product was purified by crystallization

Sources & evidence

ORD record
ord-f9981265721b440889789e1936bb4c4a
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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