Acetonitrile → HCID 178453868, compound

HRID 1662063Notes

Reaction equation

HRID 1662063 reaction equation
[NH2:1][C:2](=[N:16][OH:17])[C@@H:3]1[CH2:7][CH2:6][CH2:5][C@@H:4]1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].C(#N)C.[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22].C1CCN2C(=NCCC2)CC1>O.Cl>[S:22]=[C:21]1[O:17][N:16]=[C:2]([C@@H:3]2[CH2:7][CH2:6][CH2:5][C@@H:4]2[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])[NH:1]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 802641,1'-ThiocarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86644626HCID 86644626, compound

Product 1

HCID 178453868HCID 178453868, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of tert-butyl {(1S,2R)-2-[amino(hydroxyimino)methyl]cyclopentyl}carbamate (320 mg) and acetonitrile (8.0 ml) were added 1,1′-carbonothioyl bis(1H-imidazole) (391 mg) and DBU (787 μl) in this order, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with water (15 ml), and 1 M hydrochloric acid was added thereto to adjust the pH to about 4, followed by extraction with ethyl acetate (40 ml). The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was then removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol-chloroform) and then washed with cooled ethyl acetate (2 ml) to obtain tert-butyl [(1S,2R)-2-(5-thioxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)cyclopentyl]carbamate (160 mg) as a white solid.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with ethyl acetate (40 ml)
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was then removed by evaporation under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (3% methanol-chloroform)
  7. washwashed with cooled ethyl acetate (2 ml)

Sources & evidence

ORD record
ord-fa62ec06af344189af0b04fb0575febf
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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