3,4-dihydro-2H-pyran → HCID 69588744, compound

HRID 1796867Notes

Reaction equation

HRID 1796867 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH2:16][S:17][CH3:18])[CH:10]([OH:14])[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:19]1[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][CH2:16][S:17][CH3:18])[CH:10]([O:14][CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][O:19]1)[C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86756990HCID 86756990, compound

Product 1

HCID 69588744HCID 69588744, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 11A (1.62 g, 5.8 mmol), 3,4-dihydro-2H-pyran (0.64 mL, 70 mmol), and pyridinium p-toluenesulfonate (0.15 mL, 0.60 mmol) in dichloromethane (30 mL) was heated to 35° C. for 16 hours and concentrated. The concentrate was diluted with aqueous sodium hydroxide (0.25M, 15 mL) and extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 3 with aqueous H3PO4 (1.0M) and extracted three times with ethyl acetate. These three extracts were combined, washed sequentially with water (20 mL) and brine (20 mL), dried (MgSO4), filtered, and concentrated to provide the desired product (0.61 g). MS (APCI(+)) m/e 364 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with aqueous sodium hydroxide (0.25M, 15 mL)
  3. extractionextracted twice with ethyl acetate
  4. extractionextracted three times with ethyl acetate
  5. washwashed sequentially with water (20 mL) and brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3c218efa15594445a07168f330ceb3be
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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