Acetic Acid → HCID 21472087, compound

HRID 2294875Notes

Reaction equation

HRID 2294875 reaction equation
[CH3:1][CH:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:7](=[O:20])[CH2:6][C:5]1=[O:21])[CH3:3].CC(C)([O-])C.[K+].C(C1C=C(C(C)C)C=C(C(C)C)C=1S([N:46]=[N+:47]=[N-:48])(=O)=O)(C)C.C(O)(=O)C.C(=O)([O-])O.[Na+]>O1CCCC1>[N:46]([CH:6]1[C:5](=[O:21])[N:4]([CH:2]([CH3:1])[CH3:3])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:7]1=[O:20])=[N+:47]=[N-:48]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 3717072,4,6-Triisopropylbenzenesulfonyl azideHCID 516892Sodium BicarbonateHCID 21472092HCID 21472092, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21472087HCID 21472087, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirring solution of 1-(2-propyl)-5-(2,2,2-trifluoroethyl)-1,5-benzodiazepine-2,4-dione (440 mg, 1.46 mmole) in tetrahydrofuran (12 mL), which was cooled to -78° C. in a dry ice/acetone bath, was added dropwise potassium tert-butoxide (1M in tetrahydrofuran, 1.61 mL, 1.61 mmole). After ten minutes, 2,4,6-triisopropylbenzenesulfonyl azide (495 mg, 1.61 mmole) in tetrahydrofuran (5 mL) was added dropwise. After ten minutes, acetic acid (0.35 mL,5.84 mmole) in tetrahydrofuran (5 mL) was added in one portion and the reaction was warmed to room temperature over three hours. The reaction was poured into a solution of saturated sodium hydrogen carbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:3 ethyl acetate:hexane to give 350 mg of product identified as the axial conformer and 35 mg of the equatorial isomer. NMR data is given for the major isomer.

Workup

  1. waitAfter ten minutes
  2. waitAfter ten minutes
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel eluting with 1:3 ethyl acetate

Sources & evidence

ORD record
ord-c2043cc75a16410092b26babfa1e63c6
Source dataset
uspto-grants-1997_11
Patent number
US05691331

Reaction notes

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