Sodium hydride → t-butyl (R)-(2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepin-1-ylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate

HRID 1734305Notes

Reaction equation

HRID 1734305 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[NH:7][C:6](=[O:16])[CH2:5]1.[CH3:17][C:18]1([CH3:42])[N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:21]([CH2:30]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:20][O:19]1>CN(C=O)C>[CH3:3][N:4]1[C:10](=[O:11])[C:9]2[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=2[N:7]([CH2:30][C@@H:21]2[CH2:20][O:19][C:18]([CH3:17])([CH3:42])[N:22]2[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:6](=[O:16])[CH2:5]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 37255754-methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dioneHCID 10786336((S)-3-(Tert-butoxycarbonyl)-2,2-dimethyloxazolidin-4-YL)methyl 4-methylbenzenesulfonate

Product 1

HCID 53689955t-butyl (R)-(2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepin-1-ylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylateYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1.1 g of sodium hydride dispersion (60%) are suspended in 50 ml of DMF. 5.23 g of 4-methyl-3H-1,4-benzodiazepine-2,5(1H, 4H)-dione are added thereto so that the temperature does not exceed 35° C. and the mixture is stirred at room temperature for 90 minutes. Subsequently, a solution of 5.3 g of t-butyl (S)-2,2-dimethyl-4-(p-tolylsulfonyloxymethyl)-3-oxazolidinecaboxylate (Example 6a) in 50 ml of DMF is added thereto and the mixture is stirred at 50° C. overnight. The reaction mixture is evaporated and the residue is taken up in ethyl acetate, washed with water and dried. After evaporation of the solvent the residue is purified over silica gel with ethyl acetate/hexane (1:1). There are obtained 1.85 g of t-butyl (R)-(2,3,4,5-tetrahydro-4-methyl-2,5-dioxo-1H-1,4-benzodiazepin-1-ylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate.

Workup

  1. customdoes not exceed 35° C.
  2. stirringthe mixture is stirred at 50° C. overnight
  3. customThe reaction mixture is evaporated
  4. washwashed with water
  5. customdried
  6. customAfter evaporation of the solvent the residue
  7. customis purified over silica gel with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-afc350d2d9794845a3c166686b2326b4
Source dataset
uspto-grants-1996_07
Patent number
US05532232

Reaction notes

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