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 272135Notes

Reaction equation

HRID 272135 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 an extra amount of tetrabutylammonium fluoride in THF (54 μL, 0.054 mmol) was added. The reaction was stirred for an additional 16 hours when the reaction was complete. The reaction mixture was concentrated in vacuo and the product was purified by reverse-phase HPLC using a Phenomenex Synergi 5μ Hydro RP 80 A 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) 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); 31P (121.4 MHz, CDCl3) δ 27.7; MS (m/z) 525.2 [M−H]−.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe product was purified by reverse-phase

Sources & evidence

ORD record
ord-42e7fa1507a94b9fb1152a593ee14d63
Source dataset
uspto-grants-2008_11
Patent number
US07452901B2

Reaction notes

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