Methanol → HCID 88389311, compound

HRID 741696Notes

Reaction equation

HRID 741696 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15](/[CH:19]=[CH:20]\[CH2:21][NH:22][OH:23])[CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[CH:4][CH:3]=1.[Si]([N:28]=[C:29]=[O:30])(C)(C)C.CO>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][N:11]=[C:10]([C:13]3[CH:14]=[C:15](/[CH:19]=[CH:20]\[CH2:21][N:22]([OH:23])[C:29]([NH2:28])=[O:30])[CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 131719535HCID 131719535, compound

Product 1

HCID 88389311HCID 88389311, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 5, above (17, 0.66 g, 2.1 mmol), in THF (10 ml) was added TMSNCO (0.42 ml, 3.1 mmol) under a nitrogen atmosphere and the reaction mixture was stirred at room temperature for 1 hour. Methanol (5 ml) was then added and after stirring for 10 minutes, solvent was removed under reduced pressure. The residue was recrystallized from ethyl acetate/methanol to afford the title compound (18, 340 mg, 45% yield) as colorless solids.

Workup

  1. stirringafter stirring for 10 minutes
  2. customsolvent was removed under reduced pressure
  3. customThe residue was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-62685f29a98b49fb8e5e08f27b9498cd
Source dataset
uspto-grants-1996_09
Patent number
US05552424

Reaction notes

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