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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 711178Generated: October 30, 2026

Sodium Bicarbonate → HCID 86344810, compound

https://huagongshe.com/reaction/711178

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantTetrabutylammonium FluorideHCID 2724141—
ReactantHCID 123957994HCID 123957994—
SolventDichloromethaneHCID 6344—
SolventTetrahydrofuranHCID 8028—
ProductHCID 86344810HCID 8634481033%

Reaction Conditions

Temperature50 °C

Reaction Steps

A solution of Intermediate 61g (18 mg, 0.02 mmol) in THF (0.10 mL) was treated with tetrabutylammonium fluoride (1M in THF, 0.10 mL, 0.10 mmol) and the mixture was heated to 50° C. for 2 h. The mixture was diluted with DCM and a saturated aqueous sodium bicarbonate solution. The layers were separated and the aqueous layer was then extracted with DCM (2×). The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by HPLC (Method 6; 5-95% MeCN in H2O, 0.1% HCO2H over 25 mins) to give the title compound (5 mg, 33%). LCMS (Method 5): Rt 3.52 min, m/z 747.6 [MH+]. 1H NMR (400 MHz, d6-DMSO): 0.91 (3H, d, J=6.4 Hz), 1.26 (9H, s), 1.44-1.56 (2H, m), 1.61-1.73 (2H, m), 1.74-1.98 (4H, m), 1.99-2.12 (2H, m), 2.13 (3H, s), 2.25-2.37 (3H, m), 2.37-2.49 (5H, m, obscured by DMSO), 2.86-2.95 (1H, m), 3.12-3.19 (1H, m, obscured by water), 3.20-3.44 (1H obscured by water), 3.64 (2H, s), 4.77-4.86 (1H, m), 5.51 (1H, t, J=4.4 Hz), 6.28 (1H, s), 6.81-6.85 (1H, m), 7.05 (1H, d, J=8.6 Hz), 7.15-7.21 (3H, m), 7.24-7.30 (2H, m), 7.30-7.39 (2H, m), 7.63 (1H, d, J=10.2 Hz), 7.69 (1H, d, J=1.7 Hz), 7.95 (1H, s), 8.36 (0.1H, s).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09181242B2
Source datasetuspto-grants-2015_11
ORD IDord-2a2ead0545be4ae29e7ea69feb6c63d3
Source noteuspto-grants-2015_11