3,4-dihydro-2H-pyran → HCID 178518180, compound

HRID 46123Notes

Reaction equation

HRID 46123 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH:11]([CH2:15][CH2:16][OH:17])[C:12](=[O:14])[N:13]=1.[O:18]1[CH:23]=[CH:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH:11]([CH2:15][CH2:16][O:17][CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][O:18]2)[C:12](=[O:14])[N:13]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 178518179HCID 178518179, compound

Product 1

HCID 178518180HCID 178518180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)thiazol-4(5H)-one (3.2 g, 12.6 mmol) and p-toulenesulfonic acid (500 mg) in 3,4-dihydro-2H-pyran (10 mL) was stirred for 2 h at room temperature. The resulting mixture was diluted with CH2Cl2 (100 mL), then washed with sat'd NaH2PO4, and dried over MgSO4. After being filtered and concentrated in vacuo, the crude residue was purified by flash chromatography (3:2; Hexane:EtOAc) to give the title compound as an oil. MS (ES+): 339 (M+H)+.

Workup

  1. washwashed with sat'd NaH2PO4
  2. dry with materialdried over MgSO4
  3. filtrationAfter being filtered
  4. concentrationconcentrated in vacuo
  5. customthe crude residue was purified by flash chromatography (3:2; Hexane:EtOAc)

Sources & evidence

ORD record
ord-4d310588096c413591ea91d49146f949
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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