Deoxycholic Acid → (3.alpha.,5.beta.,12.alpha.)-3,12-dihydroxycholan-24-oic acid(3.alpha.,5.beta.,12.alpha.)-

HRID 2418969Notes

Reaction equation

[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]>C(O)=O>[OH:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[CH:19]([CH2:18][CH2:17][C@@H:16]3[C@@H:15]2[CH2:14][C@H:13]([OH:27])[C@@:12]2([CH3:28])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:24]1

Participants

Conditions

Temperature: 15 °C

Procedure

A dispersion of deoxycholic acid (1030 g; 2.63 mol) in 98% formic acid (3.72 l) was heated at 60°-70° with stirring for 2 hr. The resulting solution was allowed to cool slowly and was then left at room temperature overnight. It was then concentrated by distillation in vacuo at 40°. After 2 liters of distillate was collected, crystallization began to occur and the mixture was cooled to 15° C. The solids were then collected by filtration, washed with cold formic acid (400 ml) and dried to give 1065 g (90.5%) of 3α,12α-dihydroxycholanic acid, diformate, mp 192°-194°. Concentration of the mother liquors afforded additional material which raised the yield to about 95%.

Workup

temperatureto cool slowly
waitwas then left at room temperature overnight
concentrationIt was then concentrated by distillation in vacuo at 40°
distillationAfter 2 liters of distillate was collected
customcrystallization
filtrationThe solids were then collected by filtration
washwashed with cold formic acid (400 ml)
customdried

Sources & evidence

ORD record: ord-07ff8edd8ed740a58176dda85b9012ba
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04104285

Reaction notes

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