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

HRID 852788Notes

Reaction equation

HRID 852788 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-197af94ae56f40df8e7be4df1637475b
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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