Potassium Carbonate → (R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

HRID 352376Notes

Reaction equation

HRID 352376 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][C@H:3]1[NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].Cl[CH2:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].[K+]>[C:30]([C:29]([CH2:28][N:8]1[C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:4][C@@H:3]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:2]1=[O:1])=[O:34])([CH3:33])([CH3:32])[CH3:31]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 12043264(R)-(-)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

Product 1

HCID 12043265(R)-1-tert-butylcarbonylmethyl-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepineYield 99.8%

Reagents, catalysts & solvents 3

HCID 4875Potassium IodideCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 50 g of (R)-(−)-2-oxo-3-tert-butoxycarbonylamino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine in 200 ml of dimethylsulfoxide were added 28.1 g of 1-chloropinacolone, 28.8 g of potassium carbonate (powder), 1.15 g of potassium iodide and 1.35 g of tetrabutylammonium bromide. The mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into ice water. The precipitate thus formed was collected by filtration with suction, washed with water and then dried, whereby 63.5 g of the title compound was obtained.

Workup

  1. customThe precipitate thus formed
  2. filtrationwas collected by filtration with suction
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-71aa540e1d8e46a180281fff0427b79a
Source dataset
uspto-grants-2004_06
Patent number
US06747022B2

Reaction notes

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