Sodium Hydroxide → HCID 131724834, compound

Hexanoic acid 3-(3,4,5-trihydroxy-6-phosphonooxymethyl-tetrahydro-pyran-2-yl)-propyl ester (2.1 g, 5.25 mmol) (prepared in Example 8) was dissolved in water (50 ml) and aqueous sodium hydroxide (1M, 4 eq, 12 ml) was added and stirred for 40 minutes at room temperature after which the solution was acidified (pH˜2) with Dowex 50W X8 H+ form. The solution was washed with dichloromethane (2×100 ml) and the solvent was removed. The residue was then dissolved in a minimum of water and added dropwise to a solution of sodium acetate (1.2 eq, 0.34 g) in ethanol (150 ml) and diethyl ether (50 ml). The resulting precipitate was centrifuged and the ethanol decanted off, the residue was washed with diethyl ether (2×100 ml) and dried to give phosphoric acid mono-[3,4,5-trihydroxy-6-(3-hydroxy-propyl)-tetrahydro-pyran-2-ylmethyl] ester monosodium salt (1.01 g, 63%). 1Hnmr (500 MHz, D2O): δ 1.35-1.46 (m, 2H), 1.46-1.58 (m, 1H), 1.62-1.72 (m, 1H), 3.41-3.50 (m, 3H) 3.56 (t, J=9.0 Hz, 1H), 3.65-3.70 (m, 1H), 3.71-3.79 (m, 2H), 3.83-3.96 (m, 2H); ESMS (−ve) 301 (M−H).

1. washThe solution was washed with dichloromethane (2×100 ml)
2. customthe solvent was removed
3. dissolutionThe residue was then dissolved in a minimum of water
4. customthe ethanol decanted off
5. washthe residue was washed with diethyl ether (2×100 ml)
6. customdried

ORD record

ord-c4b5df1f60334c528a2440fe98de523f

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878690B2