Tetrabutylammonium Fluoride → 2-{4-[(1-Carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)4-methyl-hex-4-enoic acid

HRID 910501Notes

Reaction equation

HRID 910501 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:46])[CH:7]([CH2:33][CH:34]=[CH:35][CH2:36][P:37]([O:40][CH:41]([C:43]([OH:45])=[O:44])[CH3:42])([OH:39])=[O:38])[CH2:8][C:9]([CH3:32])=[CH:10][CH2:11][C:12]1[C:13]([O:25]CC[Si](C)(C)C)=[C:14]2[C:18](=[C:19]([CH3:23])[C:20]=1[O:21][CH3:22])[CH2:17][O:16][C:15]2=[O:24].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:43]([CH:41]([O:40][P:37]([CH2:36][CH:35]=[CH:34][CH2:33][CH:7]([CH2:8][C:9]([CH3:32])=[CH:10][CH2:11][C:12]1[C:13]([OH:25])=[C:14]2[C:18](=[C:19]([CH3:23])[C:20]=1[O:21][CH3:22])[CH2:17][O:16][C:15]2=[O:24])[C:6]([OH:46])=[O:5])([OH:39])=[O:38])[CH3:42])([OH:45])=[O:44]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 765461932-{4-[(1-Carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl Ester

Product 1

HCID 765461922-{4-[(1-Carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)4-methyl-hex-4-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of crude 2-{4-[(1-carboxy-ethoxy)-hydroxy-phosphoryl]-but-2-enyl}-6-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-4-methyl-hex-4-enoic acid 2-trimethylsilanyl-ethyl ester (AC-2101-59) and tetrabutylammonium fluoride in THF (1M, 54 μL, 0.054 mmol) was stirred with THF (1 mL) for 2 hours at ambient temperature, when more tetrabutylammonium fluoride in THF (54 μL, 0.054 mmol) was added. The reaction was stirred for an additional 16 hours, by which time the reaction was complete. The reaction mixture was concentrated in vacuo and the product was purified by RP HPLC using a Phenomenex Synergi 5μ Hydro RP 80A column (50×21.2 mm) with eluents of H2O, 0.1% TFA-CH3CN, 0.1% TFA to provide the product (8.0 mg) as a clear oil. 1H NMR (300 MHz, CDCl3) δ 1.51 (d, 3H, J=7 Hz), 1.79 (s, 3H), 2.05-2.40 (m, 4H), 2.11 (s, 3H), 2.49-2.71 (m, 3H), 3.38 (d, 2H, J=6 Hz), 3.76 (s, 3H), 4.85 (br s, 1H), 5.20 (s, 2H), 5.21-5.30 (m, 1H), 5.33-5.63 (m, 2H) ppm; 31P (121.4 MHz, CDCl3) δ 27.7 ppm; MS (m/z) 525.2 [M−H]−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product was purified by RP HPLC

Sources & evidence

ORD record
ord-1a598b7521d740e28f7d9a546b85e1f6
Source dataset
uspto-grants-2011_09
Patent number
US08022083B2

Reaction notes

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