Methanol → HCID 88230540, compound

HRID 1596620Notes

Reaction equation

HRID 1596620 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([NH:13][OH:14])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C[Si]([N:19]=[C:20]=[O:21])(C)C.CO>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:12][CH2:11][C@H:10]([N:13]([OH:14])[C:20]([NH2:19])=[O:21])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 70696Trimethylsilyl isocyanateHCID 88230495HCID 88230495, compound

Product 1

HCID 88230540HCID 88230540, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the compound prepared in Step 6, above (2.4 g, 12 mmol), in THF (10 ml) was added trimethylsilylisocyanate (85%, 2.4 ml, 18 mmol) and the reaction mixture was stirred at room temperature for 1.5 hours. Methanol (10 ml) was added and 10 minutes later the solvent was removed under reduced pressure to afford a white solid. Recrystallization from IPE/hexane afforded the title compound (1.6 g, 57% yield) as a colorless solid, m.p. 104.2-105.7° C.

Workup

  1. customwas removed under reduced pressure
  2. customto afford a white solid
  3. customRecrystallization from IPE/hexane

Sources & evidence

ORD record
ord-12562eb8afe7428a853f3cfea4753937
Source dataset
uspto-grants-2001_09
Patent number
US06291520B1

Reaction notes

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