Lithium Hydroxide → Deoxycholic Acid

HRID 601753

Reaction equation

[Li+].[OH-].C([O:6][C@@H:7]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:24])[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[CH2:8]1)(=O)C>O.C1COCC1.CO>[CH3:24][C@@H:17]([C@@H:16]1[C@@:25]2([CH3:34])[C@@H:26]([OH:33])[CH2:27][C@@H:28]3[C@@:29]4([CH3:32])[CH2:30][CH2:31][C@@H:7]([OH:6])[CH2:8][C@H:9]4[CH2:10][CH2:11][C@H:12]3[C@@H:13]2[CH2:14][CH2:15]1)[CH2:18][CH2:19][C:20]([OH:22])=[O:21]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of LiOH (187 mg, 4.4 mmol) in H2O (2.0 mL) was added to a solution of compound 2.1a (500 mg, 1.11 mmol) in THF (8 mL) and MeOH (8 mL). The resulting mixture was stirred for 3-4 h at 50° C. Upon complete disappearance of the starting material by TLC, the reaction mixture was concentrated under vacuum. A mixture of water (10 mL) and 3 N HCl (1 mL) were combined and cooled to 0° C. and then added to the crude product. After stirring for 1 h at 0° C., the precipitated solids were filtered and then washed with water (10 mL) and hexane (20 mL). Drying under vacuum at room temperature provided deoxycholic acid (DCA, 400 mg, 91% yield) as a white solid.

Workup

concentrationUpon complete disappearance of the starting material by TLC, the reaction mixture was concentrated under vacuum
additionA mixture of water (10 mL) and 3 N HCl (1 mL)
temperaturecooled to 0° C.
additionadded to the crude product
stirringAfter stirring for 1 h at 0° C.
filtrationthe precipitated solids were filtered
washwashed with water (10 mL) and hexane (20 mL)
customDrying under vacuum at room temperature

Sources & evidence

ORD record: ord-7ad55366cbc24ec6bacface3d5f6b48a
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902387B2

Linked notes

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