Trimethylsilyl isocyanate → HCID 9904992, compound

HRID 2082091Notes

Reaction equation

HRID 2082091 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]3[CH2:16][CH:15]([NH:17][OH:18])[CH2:14]3)[CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C[Si]([N:25]=[C:26]=[O:27])(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]3[CH2:16][CH:15]([N:17]([OH:18])[C:26]([NH2:25])=[O:27])[CH2:14]3)[CH:10]=[CH:11][CH:12]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 19779539HCID 19779539, compound

Product 1

HCID 9904992HCID 9904992, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-(4-fluorophenoxy)phenyl)-1-cyclobutylhydroxylamine from above in THF (50 mL) was added trimethylsilylisocyanate (1.64 g of 85% purity, 12.12 mmol) and the reaction was stirred for 10 min. It was then concentrated in vacuo. The resulting residue was chromatographed (silica gel; ether, methanol 96:4 to 90:10) to afford 1.60 g (50% over three steps) of N-[3-(3-(4-fluorophenoxy)phenyl)-cyclobutyl]-N-hydroxyurea as a 1:1 mixture of diastereomers.

Workup

  1. concentrationIt was then concentrated in vacuo
  2. customThe resulting residue was chromatographed (silica gel; ether, methanol 96:4 to 90:10)

Sources & evidence

ORD record
ord-5843dd7007384e789369d13a8752bc95
Source dataset
uspto-grants-1993_02
Patent number
US05187192

Reaction notes

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