Acetic Acid → HCID 11150086, compound

HRID 1863860Notes

Reaction equation

HRID 1863860 reaction equation
[Si]([O:8][CH2:9][C@@:10]1([C:26]#[C:27][Si](CC)(CC)CC)[O:14][C@@H:13]([N:15]2[C:24]3[N:23]=[C:22]([F:25])[N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[CH:16]2)[CH2:12][CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1>[C:26]([C@:10]1([CH2:9][OH:8])[O:14][C@@H:13]([N:15]2[C:24]3[N:23]=[C:22]([F:25])[N:21]=[C:19]([NH2:20])[C:18]=3[N:17]=[CH:16]2)[CH2:12][CH2:11]1)#[CH:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 59676211HCID 59676211, compound

Product 1

HCID 11150086HCID 11150086, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 22 (101 mg, 0.200 mmol) was dissolved in tetrahydrofuran (10 ml), and a solution of 1-M tetrabutylammonium fluoride in tetrahydrofuran (0.42 ml, 0.42 mmol) was added to the resultant solution, followed by stirring at room temperature for five minutes. After acetic acid (24 μl) was added to the resultant reaction mixture, the resultant mixture was concentrated under reduced pressure. The thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1), to thereby yield compound 23 (53.0 mg, 0.191 mmol, 95.7%).

Workup

  1. customreaction mixture
  2. concentrationthe resultant mixture was concentrated under reduced pressure
  3. customThe thus-obtained residue was purified by means of silica gel column chromatography (silica gel 15 ml, chloroform:methanol=40:1 to 20:1)

Sources & evidence

ORD record
ord-e08bc9c0df6740278e77a2f91a0db294
Source dataset
uspto-grants-2009_12
Patent number
US07625877B2

Reaction notes

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