Hydrochloric Acid → (6alpha-Fluoro-11beta-hydroxy-3,20-dioxo-16alpha-methyl-1,4-pregnadien-21-yl) hydrogen succinate

HRID 1581068Notes

Reaction equation

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

Participants

Conditions

Temperature: 20 °C

Procedure

Five grams of 6α-fluoro-11β,21 -dihydroxy-16α-methyl-1,4-pregnadiene-3,20-dione is refluxed in 25 ml. of pyridine with 5 g. of succinic acid anhydride for 2 hours. After cooling to 20°C., the solution is stirred into ice water, acidified with hydrochloric acid, and the thus-precipitated product is vacuumfiltered, washed with water, and dried. By recrystallization from ethyl acetate, 4.85 g. of (6α-fluoro-11β-hydroxy-3,20-dioxo-16α-methyl-1,4-pregnadien-21-yl) hydrogen succinate is obtained, m.p. 212°-214° C.

Workup

washwashed with water
customdried
customBy recrystallization from ethyl acetate, 4.85 g

Sources & evidence

ORD record: ord-97e028f0c2b24c91947e7d85d40ed6f2
Source dataset: uspto-grants-1976_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03935245

Reaction notes

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