Formic Acid → HCID 11037698, compound

HRID 2265804Notes

Reaction equation

HRID 2265804 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[CH2:13][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][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:29]([OH:31])=O.[O:32]1CCC[CH2:33]1>>[CH:33]([O:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[C@H:19]([CH2:18][C@@H:17]([O:27][CH:29]=[O:31])[C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][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)=[O:32]

Participants

4

Reactant 3

HCID 284Formic AcidHCID 8028TetrahydrofuranHCID 10133Chenodeoxycholic Acid

Product 1

HCID 11037698HCID 11037698, compoundYield 96%

Procedure

CDCA (II) (15.0 g, 38.27 mmol) was dissolved in 83 ml of tetrahydrofuran and treated with 18 drops of 70% HClO4. Formic acid (50 ml) was then added dropwise in 40 min and the resulting mixture was reacted at 54° C. for 8 h. The mixture was then concentrated under vacuum and the residue was taken up in water. The white precipitate was filtered, washed several times with water, triturated in water at 5° C. for 20 min, and dried under high vacuum to obtain 16.5 g (36.83 mmol, 96%) of pure compound (V).

Workup

  1. customthe resulting mixture was reacted at 54° C. for 8 h
  2. concentrationThe mixture was then concentrated under vacuum
  3. filtrationThe white precipitate was filtered
  4. washwashed several times with water
  5. customtriturated in water at 5° C. for 20 min
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-e5b8e9dc11274d1ca10ba6f3eed2ba40
Source dataset
uspto-grants-2010_12
Patent number
US07858608B2

Reaction notes

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