Tetrabutylammonium Fluoride → HCID 86585983, compound

HRID 1935629Notes

Reaction equation

HRID 1935629 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])[CH:16]=2)[N:11]1[CH:30]=[O:31])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[OH:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N:19]3[CH2:23][C@H:22]([CH2:24][NH:25][C:26](=[O:28])[CH3:27])[O:21][C:20]3=[O:29])[CH:16]=2)[N:11]1[CH:30]=[O:31]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86585982HCID 86585982, compound

Product 1

HCID 86585983HCID 86585983, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred, ice cold mixture of the product from Step 10 (0.35 g, 0.78 mmol) and THF (20 ml), under nitrogen is treated, dropwise stirring 3 min, with 1 M tetrabutylammonium fluoride in THF (3.31 ml). It is kept in the ice bath for 5 min and at ambient temperature for 2 h. It is then diluted with EtOAc, washed with water and brine, dried (MgSO4) and concentrated. Chromatography of the residue over silica gel with acetone gave 0.20 g of the titled product: mp 132-136° C.; HRMS (FAB) calcd for C16H19N3O5+H 334.1403, found 334.1418; 1H NMR [300 MHz, (CD3)2SO] δ1.81 (s, 3H), 2.80, 3.01 (m, m, 1H), 3.38 (m, 5H), 3.69 (m, 1H), 4.06 (m, 1H), 4.45 (m, 1H), 4.68 (m, 1H), 4.89, 5.17 (t, t, 1H), 7.26 (m, 1H), 7.38, 7.86 (d, d, 1H), 7.48 (m, 1H), 8.24 (t, 1H), 8.44, 8.95 (s, s, 1H).

Workup

  1. additionunder nitrogen is treated
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b91aff42eb2c4a3aaa9c1d1fe985e313
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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