Methanol → HCID 19426801, compound

HRID 741691Notes

Reaction equation

HRID 741691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][CH:11]([C:13]3[CH:14]=[C:15]([C:19]#[C:20][CH:21]([NH:23][OH:24])[CH3:22])[CH:16]=[CH:17][CH:18]=3)[O:10][N:9]=2)=[CH:4][CH:3]=1.[Si]([N:29]=[C:30]=[O:31])(C)(C)C.CO>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:12][CH:11]([C:13]3[CH:14]=[C:15]([C:19]#[C:20][CH:21]([N:23]([OH:24])[C:30]([NH2:29])=[O:31])[CH3:22])[CH:16]=[CH:17][CH:18]=3)[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 19426806HCID 19426806, compound

Product 1

HCID 19426801HCID 19426801, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 2, above (11, 1.9 g, 5.8 mmol), in THF (10 ml) was added TMS-NCO (1.1 ml, 8.8 mmol), and the reaction mixture was stirred at room temperature for 2 hours. To the mixture was added methanol (5 ml) and the reaction mixture was stirred for 10 minutes and then solvent was removed by evaporation. The residue was chromatographed on silica gel (5% methanol/ethyl acetate) to give the crude title compound. Recrystallization from methanol/n-hexane/ethyl acetate afforded the title compound (12, 1.5 g, 67% yield) as colorless solids.

Workup

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customsolvent was removed by evaporation
  3. customThe residue was chromatographed on silica gel (5% methanol/ethyl acetate)
  4. customto give the crude title compound
  5. customRecrystallization from methanol/n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-6b43a4bc6f394cc9a0b71c0fe9ae36d8
Source dataset
uspto-grants-1996_09
Patent number
US05552424

Reaction notes

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