Hydrochloric Acid → HCID 86589030, compound

HRID 897050Notes

Reaction equation

HRID 897050 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].[CH3:28][C:29]1[CH:33]=[CH:32][S:31][C:30]=1[C:34](Cl)=[O:35].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:34]([C:30]1[S:31][CH:32]=[CH:33][C:29]=1[CH3:28])=[O:35])[C:23]([OH:25])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 27376053-Methyl-2-thenoyl ChlorideHCID 49822397HCID 49822397, compound

Product 1

HCID 86589030HCID 86589030, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 (20 g) is dissolved in pyridine (50 mL) and cooled to 0° C. 3-Methylthiophene-2-carbonyl chloride (9.39 g) is added and the reaction 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 is followed by flash column chromatography on silica gel eluting with DCM-methanol (25:1) to afford 3-methylthiophene-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 0.90 (3H, d), 0.95 (3H, s), 1.40 (3H, s), 2.40 (3H, s).

Workup

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

Sources & evidence

ORD record
ord-900f25748e074f5498dc60ab02250d94
Source dataset
uspto-grants-2005_07
Patent number
US06921757B2

Reaction notes

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