Hydrochloric Acid → HCID 86589029, compound

HRID 897048Notes

Reaction equation

[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:27])[CH:9]([CH:10]4[CH2:11][C@H:12]([F:21])[C:13]5[C@@:18]([CH3:19])([C@:2]124)[CH:17]=[CH:16][C:15](=[O:20])[CH:14]=5)[CH2:8][C@@H:7]([CH3:22])[C@:6]3([OH:26])[C:23]([OH:25])=[O:24].[O:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](Cl)=[O:34].Cl.C(Cl)Cl>N1C=CC=CC=1>[O:1]1[C@H:3]2[CH2:4][C@@:5]3([CH3:27])[CH:9]([CH:10]4[CH2:11][C@H:12]([F:21])[C:13]5[C@@:18]([CH3:19])([C@:2]124)[CH:17]=[CH:16][C:15](=[O:20])[CH:14]=5)[CH2:8][C@@H:7]([CH3:22])[C@:6]3([O:26][C:33]([C:29]1[O:28][CH:32]=[CH:31][CH:30]=1)=[O:34])[C:23]([OH:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

(6S,9S,10S,11S,13S,16R,17R)-9,11-Epoxy-6-fluoro-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-17-carboxylic acid (5 g) is dissolved in pyridine (15 mL) and cooled to 0° C. 2-Furoyl chloride (1.82 g) is added and the reaction mixture is stirred at room temperature. After 2 hours, the reaction mixture is added dropwise to a vigorously stirred solution of 6M HCl. DCM is added, the phases are separated and the organic phase is washed with water and brine. After drying over magnesium sulphate, evaporation affords furan-2-carboxylic acid (6S,9S,10S,11S,13S,16R,17R)-9,11-epoxy-6-fluoro-17-carboxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester. Selected 1H-NMR signals (CDCl3) δ 6.30 (1H, dd), 6.5 (2H, m), 6.55 (1H, d), 7.20-7.65 (m, 2H).

Workup

customthe phases are separated
washthe organic phase is washed with water and brine
dry with materialAfter drying over magnesium sulphate, evaporation

Sources & evidence

ORD record: ord-2f42d4625f0a46c29f02080c4b63404d
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921757B2

Reaction notes

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