1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 91275966, compound

HRID 2389497Notes

Reaction equation

HRID 2389497 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.C1CCN2C(=NCCC2)CC1.[C:30]([O:34][C:35](=[O:40])[NH:36][CH2:37][CH2:38]Br)([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[C:11]([O:10][C:8](=[O:9])[CH2:7][N:6]1[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=[C:2]1[S:1][CH2:38][CH2:37][NH:36][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:40])([CH3:13])([CH3:14])[CH3:12]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 178451223HCID 178451223, compound

Product 1

HCID 91275966HCID 91275966, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 1.31 g, 4.97 mmol) in dry THF (2.6 ml) cooled to 0° C. is added a solution of DBU (756.6 mg, 742.5 μl, 0.47 mmol) in dry THF (1 ml). This yields a paste that is diluted with dry THF (2.5 ml). A solution of (2-bromo-ethyl)-carbamic acid tert-butyl ester (1.17 g, 5.22 mmol) in dry THF (2.6 ml) is then added and the resulting mixture is allowed to stir for 2 h. The solvent is removed under reduced pressure and saturated aqueous KH2PO4 solution (50 ml) is added. The product is extracted with AcOEt (150 ml), the organic phase is washed once with water and once with brine and dried over Na2SO4. The solvent is removed in vacuo and the crude mixture is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:12), yielding the title compound (1.41 g) in 69% as a colourless oil: tR=2.35 min (LC-2), ESI-MS (pos.): m/z 408.27 [M+H]+.

Workup

  1. customThis yields a paste that
  2. customThe solvent is removed under reduced pressure and saturated aqueous KH2PO4 solution (50 ml)
  3. additionis added
  4. extractionThe product is extracted with AcOEt (150 ml)
  5. washthe organic phase is washed once with water and once with brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent is removed in vacuo
  8. customthe crude mixture is purified by flash chromatography on silica-gel (AcOEt/heptane, 1:12)

Sources & evidence

ORD record
ord-9632ebf6880d4061ae44bfbde76bf318
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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