Hydrochloric Acid → HCID 24984260, compound

HRID 1724069Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][N:15]3[CH2:19][C:18]4([CH2:28][CH2:27][C:22]5(OCC[O:23]5)[CH2:21][CH2:20]4)[O:17][C:16]3=[O:29])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][N:15]3[CH2:19][C:18]4([CH2:20][CH2:21][C:22](=[O:23])[CH2:27][CH2:28]4)[O:17][C:16]3=[O:29])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(4′-Fluoro-biphenyl-4-ylmethyl)-1,9,12-trioxa-3-aza-dispiro[4.2.4.2]tetradecan-2-one (50 mg, 0.126 mmol) and 10% HCl (2 mL) were mixed in THF. The reaction mixture was heated at 60° C. for 3 hours. The reaction mixture was quenched with saturated NaHCO3 aqueous solution until PH=8. THF was removed under reduced pressure, and the aqueous phase was extracted with DCM (3×3 mL). The combined organic phases were dried over anhydrous sodium sulfate and condensed in vacuo. The residue was purified on silica gel eluting with 10˜35% ethyl acetate in hexane to give the product as a white solid (35 mg, 78%). 1H NMR (300 MHz, CDCl3): δ (ppm) 7.57 (m, 4H), 7.36 (d, 2H), 7.14 (t, 2H), 4.84 (s, 2H), 3.96 (m, 2H), 3.18 (s, 2H), 2.01 (m, 4H), 1.83 (m, 2H).

Workup

customThe reaction mixture was quenched with saturated NaHCO3 aqueous solution until PH=8
customTHF was removed under reduced pressure
extractionthe aqueous phase was extracted with DCM (3×3 mL)
dry with materialThe combined organic phases were dried over anhydrous sodium sulfate and condensed in vacuo
customThe residue was purified on silica gel eluting with 10˜35% ethyl acetate in hexane

Sources & evidence

ORD record: ord-8157fbe5fbd340c3ad3239632a7f08d0
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07485722B2

Reaction notes

Loading…