Tetrabutylammonium Fluoride → HCID 60207719, compound

HRID 1776142Notes

Reaction equation

HRID 1776142 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[C:19]([O:23][C:24](=[O:48])[NH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33](=[O:47])[CH2:34]/[CH:35]=[CH:36]/[CH2:37][CH2:38][O:39][Si](C(C)(C)C)(C)C)([CH3:22])([CH3:21])[CH3:20]>C1COCC1.CCOCC>[OH:39][CH2:38][CH2:37]/[CH:36]=[CH:35]/[CH2:34][C:33]([NH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:24](=[O:48])[O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:47]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70230367(E)-tert-butyl2-(6-(tert-butyldimethylsilyloxy)hex-3-enamido)phenylcarbamate

Product 1

HCID 60207719HCID 60207719, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A TBAF (4.46 g, 17.06 mmol) in THF was added to a solution of (E)-tert-butyl2-(6-(tert-butyldimethylsilyloxy)hex-3-enamido)phenylcarbamate (6.17 g, 14.2 mmol) in THF (180 mL) at 0° C. for 0.5 hour, then the mixture was stirred at RT for 12 hours. The reaction mixture was diluted with ether (500 mL) and washed with brine (3×200 mL), the organic layer was dried over Na2SO4, filtered and concentrated to give the desired compound of (E)-tert-butyl 2-(6-hydroxyhex-3-enamido)phenylcarbamate (10) (2.38 g, 52%) as a yellow oil after purification by column chromatography on silica gel (eluent: PE:EA=1:1). 1H NMR (300 MHz, CDCl3): δ 1.475 (S, 9H), 2.292 (q, 2H), 3.096 (d, 2H), 3.652 (t, 2H), 5.655-5.701 (m, 2H), 6.996-7.124 (m, 2H), 7.310-7.380 (m, 2H), 7.482 (d, J=7.8 Hz, 1H), 8.652 (s, 1H); LC-MS found 321 (M+H)+.

Workup

  1. washwashed with brine (3×200 mL)
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7c865e36218b46acad2a15c10a54cf14
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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