Tetrabutylammonium Fluoride → HCID 86727509, compound

HRID 519125Notes

Reaction equation

HRID 519125 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:42])([C:12]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([F:31])([F:30])[F:29])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:41])[C:19](=[O:40])[N:20](COCC[Si](C)(C)C)[N:21]=2)=[CH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:42])([C:12]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]([F:30])([F:29])[F:31])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:41])[C:19](=[O:40])[NH:20][N:21]=2)=[CH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86727510HCID 86727510, compound

Product 1

HCID 86727509HCID 86727509, compoundYield 45%

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methyl-3-{1-[4-methyl-3-oxo-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-vinyl}-azetidine-1-carboxylic acid tert-butyl ester (1.214 g, 1.662 mmol) and tetrabutylammonium fluoride (1M in THF, 22.9 mL, 22.9 mmol) was stirred at 80° C. overnight. The reaction was cooled to ambient temperature. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel (eluting with 0-10% EtOAc in petroleum ether) to give 3-methyl-3-[1-(4-methyl-3-oxo-7-trifluoromethyl-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-vinyl]-azetidine-1-carboxylic acid tert-butyl ester (0.330 g, 45%). 1H NMR (CDCl3, 400 MHz): δ 8.25 (s, 1H), 7.35 (s, 1H), 6.66 (s, 1H), 5.46 (s, 1H), 5.15 (s, 1H), 4.7 (m, 2H), 4.6 (m, 1H), 3.95 (m, 1H), 3.86 (m, 1H), 3.65 (m, 2H), 1.55 (m, 3H), 1.50 (m, 3H), 1.40 (s, 9H). LC/MS (Table 1, Method 25) Rt=0.923 min; MS m/z: 503 [M+Na]+.

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica gel (eluting with 0-10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-a2d0e46e69d24235845196dd46b5f216
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

Loading…