Sodium Bicarbonate → (3R)-2-oxo-3-tert-butoxycarbonylamino-5-[(1S)-2-pinen-10-yl]-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 1979470

Reaction equation

HRID 1979470 reaction equation
C(=O)(O)[O-].[Na+].Cl[CH2:7][C:8]1[C@H:9]2[CH2:14][CH:11]([CH2:12][CH:13]=1)[C:10]2([CH3:16])[CH3:15].[O:17]=[C:18]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[NH:21][CH2:20][C@H:19]1[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>CO>[O:17]=[C:18]1[NH:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[N:21]([CH2:7][C:8]2[C@H:9]3[CH2:14][CH:11]([CH2:12][CH:13]=2)[C:10]3([CH3:16])[CH3:15])[CH2:20][C@H:19]1[NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12988641(R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineHCID 57140078(1s)-10-Chloro-2-pinene

Product 1

HCID 70239618(3R)-2-oxo-3-tert-butoxycarbonylamino-5-[(1S)-2-pinen-10-yl]-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 61.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium bicarbonate (2.02 g) and (1s)-10-chloro-2-pinene (4.1 g) were added to a solution of (R)-2-oxo-3-tert-butoxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (2.22 g) in anhydrous methanol (40 ml), and the mixture was refluxed overnight. The reaction mixture was concentrated under reduced pressure, water (200 ml) was added, and extracted with ethyl acetate (200 ml) twice. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=4:1), to thereby obtain 2.03 g of the titled compound.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water (200 ml)
  3. additionwas added
  4. extractionextracted with ethyl acetate (200 ml) twice
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography(n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-847d882c8ab7426e9a72ca5617f6ae22
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Linked notes

Loading…