Tetrabutylammonium Fluoride → HCID 70171848, compound

HRID 1934319Notes

Reaction equation

HRID 1934319 reaction equation
[CH2:1]([O:8][C:9](=[O:38])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C@@H:18]([N:20]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:21][CH2:22][O:23][Si](C(C)(C)C)(C)C)[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:8][C:9](=[O:38])[CH2:10][CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][C@@H:18]([N:20]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:21][CH2:22][OH:23])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70171162HCID 70171162, compound

Product 1

HCID 70171848HCID 70171848, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of (5Z,10S)-(−)-N-tert-butoxycarbonyl-N-[2-tert-butyldimethylsilyloxyethyl]-10-amino-5-undecenoic acid benzyl ester (8) (100 mg, 0.18 mmol) in 1 mL of THF was added 0.2 mL of a 1M THF solution of tetrabutylammonium fluoride. The mixture was stirred at rt for 16 h, then concentrated, and purified by flash chromatography (11 mm×6″ column, eluted with 20% v/v EtOAc/hexane) yielding 76 mg of the title compound (9) as a colorless oil (0.17 mmol, 97% yield). 1H NMR (conformeric mixture, 500 MHz, C6D6): δ7.23-7.20 (m, 1H, ArH), 7.13-6.98 (m, 4H, ArH), 5.39-5.33 (m, 1H, RCH═CHR′), 5.32-5.26 (m, 1H, RCH═CHR′), 5.01 (s, 2H, ArCH2O2CR), 3.85-3.78 (m, 0.5H, NCHCH3), 3.76-3.50 (m, 2.5H, NCHCH3 and OCH2CH2N), 3.21-3.00 (m, 2H, OCH2CH2N), 2.15 (t, J=7.3 Hz, 2H, RO2CCH2), 2.01-1.90 (m, 4H, CH2CH═CHCH2), 1.63 (p, J=7.3 Hz, 2H, RO2CCH2CH2), 1.42 (s, 9H, Boc), 1.31-1.20 (m, 3H, CHaHbCH2CHN), 1.16-1.05 (m, 1H, CHaHbCH2CHN), 0.93-0.82 (m, 3H NCHCH3).

Workup

  1. concentrationconcentrated
  2. custompurified by flash chromatography (11 mm×6″ column
  3. washeluted with 20% v/v EtOAc/hexane)

Sources & evidence

ORD record
ord-b671fe4bbd374429bfcb4f6bf22ca99c
Source dataset
uspto-grants-2002_05
Patent number
US06384026B1

Reaction notes

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