Tetrabutylammonium Fluoride → HCID 54009194, compound

HRID 1604002Notes

Reaction equation

HRID 1604002 reaction equation
C[O:2][C:3]([C:5]1[O:6][C@@H:7]([C:36](=[O:55])[N:37]([CH2:41][CH2:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[CH:45][CH:44]=2)[CH2:38][CH2:39][CH3:40])[C@@H:8]([NH:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[C@H:9]([O:11][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:46]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:45]=[CH:44][C:43]([CH2:42][CH2:41][N:37]([CH2:38][CH2:39][CH3:40])[C:36]([C@@H:7]2[O:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][C@@H:9]([OH:11])[C@H:8]2[NH:29][C:30](=[O:35])[C:31]([F:32])([F:33])[F:34])=[O:55])=[CH:48][CH:47]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86754846HCID 86754846, compound

Product 1

HCID 54009194HCID 54009194, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4R,5R,6R)-6-[(2-biphenyl-4-yl-ethyl)propylcarbamoyl]-4-(tertbutyldiphenylsilanyloxy)-5-(2,2,2-trifluoroacetylamino)-5,6-dihydro-4-H-pyran-2-carboxylic acid methyl ester (1.03 g) in tetrahydrofuran (5.5 ml) was added a solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (1.45 ml of a 1M solution). The orange solution was stirred at room temperature for 4 hours before the solvent was removed in vacuo to give an orange gum. This was dissolved in ethyl acetate (50 ml) and washed with water (2×40ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent was removed in vacuo and the residue was chromatographed over silica (Merck 7734, 65 g) and dichlormethane/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 foam (0.64 g). 1H NMR (250 MHz, CDCl3 rotamers) 7.63-7.24 (9H, m), 6.96+6.92 (1H, 2×d, J=8 Hz), 6.13+6.06 (1H, 2×d, J=4 Hz), 5.16+4.86 (1H, 2×d, J=7, 5 Hz), 4.72+4.58 (1H, 2×m), 4.3 (1H, m), 3.82+3.79 (3H, 2×s), 3.78-3.23 (4H, m), 3.02+2.87 (2H, 2×t, J=8 Hz), 2.90+2.78 (2H, 2×broad s), 1.82-1.50(2H, m), 0.96+0.92 (3H, 2×t, J=8 Hz).

Workup

  1. customwas removed in vacuo
  2. customto give an orange gum
  3. washwashed with water (2×40ml)
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  5. customthe solvent was removed in vacuo
  6. customthe residue was chromatographed over silica (Merck 7734, 65 g) and dichlormethane/methanol (95:5 v/v) as the eluant
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-5f8ca6f828f341e7bdff18df0b44eb8b
Source dataset
uspto-grants-1999_11
Patent number
US05990156

Reaction notes

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