Sulfuric Acid → HCID 178422863, compound

HRID 2360288Notes

Reaction equation

HRID 2360288 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][C:11]([CH2:19][CH2:20][OH:21])([CH2:15][C:16]([CH3:18])=[CH2:17])[C:12](=[O:14])[N:13]=1.OS(O)(=O)=O>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][C:11]2([CH2:19][CH2:20][O:21][C:16]([CH3:18])([CH3:17])[CH2:15]2)[C:12](=[O:14])[N:13]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 178441215HCID 178441215, compound

Product 1

HCID 178422863HCID 178422863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)-5-(2-methylallyl)thiazol-4(5H)-one (120 mg) in CH2Cl2 (3 mL) was added concentrated H2SO4 (200 uL). The resulting mixture was stirred for 16 h, then concentrated in vacuo. The residue was treated with sat'd NaH2PO4 and extracted with CH2Cl2. The organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as solid. MS (ES+): 309 (M+H)+. The diastereomers were separated using standard HPLC methods described within this text.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with sat'd NaH2PO4
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (4:1; Hexane:EtOAc)

Sources & evidence

ORD record
ord-d2eafd8bd38f4b9bb0f51a2ed8913e9d
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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