Sodium Bicarbonate → HCID 25133550, compound

HRID 1889124Notes

Reaction equation

[Si]([O:18][C@H:19]1[CH2:26][CH2:25][CH2:24][O:23][CH2:22][O:21][CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([O-])(O)=O.[Na+]>C1COCC1>[C@H:19]1([OH:18])[CH2:26][CH2:25][CH2:24][O:23][CH2:22][O:21][CH2:20]1

Participants

Conditions

Temperature: 23 °C

Procedure

Compound 7a (0.27 g, 0.74 mmol) was dissolved in dry THF (5 mL) and TBAF (1.0 M solution in THF, 0.81 mL, 0.81 mmol) was added. The resulting mixture was stirred at 23° C. overnight, afterward a saturated solution of NaHCO3 was added, the solvent was removed and the aqueous phase was extracted with EtOAc. The organic extracts were dried and evaporated and the residue was purified by flash-chromatography (EtOAc) to afford 76 mg (77%) of 8a as a colourless oil: [α]D20, −12.6 (c 1.6, CHCl3); 1H NMR (CDCl3) δ 4.65 (d, J=6.0 Hz, 1H), 4.57 (d, J=6.0 Hz, 1H), 4.92-3.81 (m, 2H), 3.75-3.60 (m, 2H), 3.55 (dd, J=3.4, 12.1 Hz, 1H), 2.96 (bs, 1H), 1.95-1.69 (m, 3H), 1.65-1.53 (m, 1H); 13C NMR (CDCl3) δ 94.9, 73.7, 69.3, 68.2, 30.2, 24.7.

Workup

customthe solvent was removed
extractionthe aqueous phase was extracted with EtOAc
customThe organic extracts were dried
customevaporated
customthe residue was purified by flash-chromatography (EtOAc)

Sources & evidence

ORD record: ord-ca66ad4a918f4aa482248a9e02e94af5
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501961B2

Reaction notes

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