Tetrabutylammonium Fluoride → HCID 86004379, compound

HRID 1867525Notes

Reaction equation

HRID 1867525 reaction equation
[CH2:1]([O:8][C:9]([N:11]([C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=1)[CH2:12][CH2:13]OS(CC1C=CC(C)=CC=1)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-:33].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:8][C:9](=[O:10])[N:11]([C:26]1[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=1)[CH2:12][CH2:13][F:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86604703HCID 86604703, compound

Product 1

HCID 86004379HCID 86004379, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.9 g (6 mmol) toluene-4-methanesulfonic acid 2-[benzyloxycarbonyl-(4-bromo-phenyl)-amino]-ethyl ester are dissolved in 100 mL THF and stirred for 18 hours at room temperature after addition of a 1 M solution of tetrabutyl-ammonium fluoride in THF. The reaction mixture is poured onto ice and extracted with tertbutyl-methyl ether and a saturated aqueous solution of sodium bicarbonate. The combined organic phases are washed with brine, dried with sodium sulfate and evaporated to dryness. The crude product is column chromatographed (petroleum ether/ethyl acetate 4:1) to yield 920 mg desired product as a yellow resin. MS(ES+): 352 (M+1).

Workup

  1. additionThe reaction mixture is poured onto ice
  2. extractionextracted with tertbutyl-methyl ether
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried with sodium sulfate
  5. customevaporated to dryness
  6. customchromatographed (petroleum ether/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-e02772981fb64336a92f9f84cf0cbca8
Source dataset
uspto-grants-2009_12
Patent number
US07632851B2

Reaction notes

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