Tetrabutylammonium Fluoride → HCID 86701111, compound

HRID 1396258Notes

Reaction equation

HRID 1396258 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH2:18][O:19][Si](C(C)(C)C)(C)C)[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:27]([CH2:35][CH2:36][F:37])[C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[S:14]2)[C@H:10]1[O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[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@@H:9]1[C@@H:17]([CH2:18][OH:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:27]([CH2:35][CH2:36][F:37])[C:28](=[O:34])[O:29][C:30]([CH3:32])([CH3:31])[CH3:33])[S:14]2)[C@H:10]1[O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86701109HCID 86701109, compound

Product 1

HCID 86701111HCID 86701111, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl (3aR,5R,6S,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl(2-fluoroethyl)carbamate (1.36 g, 2.06 mmol) in THF (30 mL) was treated with tetrabutylammonium fluoride (1.1 g, 4.2 mmol) for 2 hrs at room temperature. The reaction mixture was quenched with H2O (10 mL), extracted with ethyl acetate (3×50 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 10%-20% ethyl acetate in petroleum ether to provide compound 71 as a pale yellow oil (600 mg, 53%). (ES, m/z) [M+H]+ 546.8; 1H NMR (300 MHz, CDCl3) δ 7.24-7.43 (m, 10H), 6.09-6.11 (d, J=4.2 Hz, 1H), 4.60-4.66 (m, 2H), 4.50-4.54 (m, 1H), 4.46-4.47 (m, 1H), 4.40-4.45 (m, 2H), 4.27-4.39 (m, 2H), 4.12-4.22 (m, 2H), 3.72-3.79 (m, 1H), 3.67-3.71 (m, 1H), 3.55-3.63 (m, 1H), 3.40-3.45 (m, 1H), 1.54 (s, 9H).

Workup

  1. customThe reaction mixture was quenched with H2O (10 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give a residue, which
  6. customwas purified by a silica gel column
  7. washeluting with 10%-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-f156fbb562dd4ad2a81ce8a4ca5d72de
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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