Tetrabutylammonium Fluoride → HCID 57128419, compound

HRID 1604004Notes

Reaction equation

HRID 1604004 reaction equation
[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:30])[N:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:31]([O:33]C)=[O:32])=[CH:7][C@@H:6]1[O:35][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([NH:4][C@H:5]1[C@H:10]([C:11](=[O:30])[N:12]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[CH2:13][CH2:14][CH3:15])[O:9][C:8]([C:31]([OH:33])=[O:32])=[CH:7][C@@H:6]1[OH:35])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57276034HCID 57276034, compound

Product 1

HCID 57128419HCID 57128419, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

To a solution of (4S,5S,6R)-5-acetylamino-4-(tert-butyldiphenylsilanyloxy)-6-[(2-biphenyl-4-yl-ethyl)propylcarbamoyl]-5,6-dihydro-4H-pyran-2-carboxylic acid, methyl ester (1.58 g) in anhydrous tetrahydrofuran (15 ml) was added a solution of tetra-n-butylammonium fluoride in anhydrous tetrahydrofuran (2.42 ml of a 1N solution) and the reaction was stirred for 16 hours at 23° C. The solvent was then removed in vacuo and the residue was suspended in brine and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried over anhydrous magnesium sulphate and the solvent was removed in vacuo. The residue was chromatographed over silica (Merck 9385, 20 g) using medium pressure (ca 4 psi) and dichloromethane/methanol (95:5 v/v) as the eluant. The required fractions were combined and the solvent removed in vacuo to give the title compound as a white solid (0.91 g). 1H NMR (250 MHz, D6 -DMSO rotamers) 8.05 (1H, d, J=8 Hz), 7.63 (4H, m), 7.45 (2H, m), 7.34 (3H, m), 5.92+5.89 (1H, 2×d, J=3 Hz), 5.32 (1H, d, J=6 Hz), 5.01+4.97 (1H, 2×d, J=8 Hz), 4.28 (1H, m), 3.94 (1H, m), 3.73+3.68 (3H, 2×s), 3.45 (1H, m), 3.24 (1H, m), 2.96 (1H, m), 2.76 (1H, m), 1.82+1.79 (3H, 2×s), 1.57 (1H, m), 1.46 (1H, m), 0.83 (0.83(3H, m), Mass analysis: C27H32N2O6. Required: C, 67.48; H, 6.71; N, 5.83. Found: C, 67.08; H, 6.61; N, 5.60.

Workup

  1. customThe solvent was then removed in vacuo
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  4. customthe solvent was removed in vacuo
  5. customThe residue was chromatographed over silica (Merck 9385, 20 g)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-61e6cbc23be54d9b993428ba9e8b0907
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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