Tetrahydrofuran → HCID 86591422, compound

HRID 970324Notes

Reaction equation

HRID 970324 reaction equation
[CH3:1][C:2]([NH:5][C:6]([C:8]1[CH:9]=[C:10](C#C[Si](C)(C)C)[C:11]2[C:12](=[O:22])[C:13]3[C:18]([NH:19][C:20]=2[CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:7])([CH3:4])[CH3:3].[CH2:29]1COC[CH2:30]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[CH3:3][C:2]([NH:5][C:6]([C:8]1[C:9]([C:29]#[CH:30])=[CH:10][C:11]2[C:12](=[O:22])[C:13]3[C:18]([NH:19][C:20]=2[CH:21]=1)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:7])([CH3:1])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 68559959HCID 68559959, compound

Product 1

HCID 86591422HCID 86591422, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A one dram vial was charged with compound 145A (13 mg, 0.033 mmol), THF (0.5 mL) and TBAF (33 L, 0.033 mmol) under argon. The reaction mixture was stirred at RT for 20 min., and then diluted with EtOAc (10 mL), washed with sat. NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The organic layer was dried over MgSO4 and concentrated in vacuo to give 145B as a yellow solid (12 mg). HPLC retention time=2.74 min. (Condition A), M+=319.

Workup

  1. washwashed with sat. NaHCO3 (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef91ac04f6d440439cf140e885b5a74a
Source dataset
uspto-grants-2007_12
Patent number
US07312209B2

Reaction notes

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