Tetrabutylammonium Fluoride → HCID 86677885, compound

HRID 1499962Notes

Reaction equation

HRID 1499962 reaction equation
[C:1]([C:4]1[C:5]([O:30][CH2:31][CH3:32])=[C:6]([CH:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:13][O:14][Si](C(C)(C)C)(C)C)[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:4]1[C:5]([O:30][CH2:31][CH3:32])=[C:6]([CH:12]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])[CH2:13][OH:14])[C:7]([F:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86677884HCID 86677884, compound

Product 1

HCID 86677885HCID 86677885, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Tert-Butyl (1-(3-acetyl-5-chloro-2-ethoxy-6-fluorophenyl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)carbamate (500 mg, 1.0 mmol) (from Step 7) was stirred in tetrahydrofuran (10 mL) and a 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (1.5 mL) was added. The mixture was stirred at rt for 30 minutes and evaporated. Purification on silica gel using ethyl acetate in hexanes (0-50%) gave the desired compound 238 mg, 60%. LCMS calculated for C17H23ClFNO5Na (M+Na)+: m/z=398.1; found: 398.1.

Workup

  1. customevaporated
  2. customPurification on silica gel

Sources & evidence

ORD record
ord-d66ce072f5e243948f525004522bef68
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…