Sulfuric Acid → HCID 178422863, compound

HRID 1158100Notes

Reaction equation

HRID 1158100 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-48fa1a97914144a09b433c17ff9ba297
Source dataset
uspto-grants-2010_10
Patent number
US07807700B2

Reaction notes

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