Sodium hydride → HCID 53689955, compound

HRID 257277Notes

Reaction equation

HRID 257277 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 53689955HCID 53689955, compoundYield 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-e95bf2694e4243db99fda9de883c09a4
Source dataset
uspto-grants-1993_11
Patent number
US05260307

Reaction notes

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