Hydrochloric Acid → HCID 86757163, compound

HRID 1385625Notes

Reaction equation

[CH3:1][C:2]1([CH3:30])[C@@H:26]([OH:27])[CH2:25][CH2:24][C@@:23]2([CH3:28])[C@H:3]1[CH2:4][CH2:5][C:6]1[C:7]3[C@:19]([CH3:29])([CH2:20][CH2:21][C:22]=12)[C@@H:10]([C@H:11]([CH3:18])[O:12][CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[CH2:9][CH:8]=3.[C:31]1(=[O:37])[O:36][C:34](=[O:35])[CH2:33][CH2:32]1.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:34]([OH:36])(=[O:35])[CH2:33][CH2:32][C:31]([O:27][C@H:26]1[CH2:25][CH2:24][C@@:23]2([CH3:28])[C@@H:3]([CH2:4][CH2:5][C:6]3[C:7]4[C@:19]([CH3:29])([CH2:20][CH2:21][C:22]=32)[C@@H:10]([C@H:11]([CH3:18])[O:12][CH2:13][CH:14]=[C:15]([CH3:16])[CH3:17])[CH2:9][CH:8]=4)[C:2]1([CH3:1])[CH3:30])=[O:37]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (3β,5α,20S)-4,4-dimethyl-22-oxacholesta-8,14,24-trien-3-ol (Example 1; 0.50 g), dry pyridine (8 ml), succinic anhydride (3.0 g), and 4-dimethylaminopyridine (20 mg) was heated at 60° C. overnight. After cooling the reaction mixture was poured into a 0.1 M aqueous solution of hydrochloric acid and the product extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate, and concentrated under reduced pressure. Column chromatography afforded (3β,5α,20S)-4,4-dimethyl-22-oxacholesta-8,14,24-trien-3-ol hydrogen butanedioate (0.35 g). M.p. 60-67° C.

Workup

temperatureAfter cooling the reaction mixture
extractionthe product extracted into ethyl acetate
washThe combined organic phases were washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ddfa31f434e34438ab64bd191ee93b20
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262282B1

Reaction notes

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