Lithocholic Acid → Cholan-24-oic acid

HRID 618606

Reaction equation

HRID 618606 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:27])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23](O)[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(OC(=O)C)(=O)C>[C:5]([OH:7])(=[O:6])[CH2:4][CH2:3][C@H:2]([C@@H:8]1[C@:12]2([CH3:27])[C@H:11]([C@H:16]3[C@H:15]([CH2:14][CH2:13]2)[C@:20]2([CH3:26])[CH:19]([CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:18][CH2:17]3)[CH2:10][CH2:9]1)[CH3:1]

Participants

3

Reactant 1

HCID 9903Lithocholic Acid

Product 1

HCID 9548797Cholan-24-oic acidYield 50%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 1 g of the lithocholic acid dimer prepared by the inventors, viz. bis(5(-cholan-24-oic-3(-yl) sebacate, in 6 ml of acetic anhydride was heated to 120° C. in an oil bath for 1 h. The solvent was partially removed and the mixed anhydride prepolymer was allowed to crystallize at -10° C. The product was filtered out, washed with a small amount of cold acetic anhydride and dried under vacuum at room temperature for two days. The requested bis (5(-cholan-24-oic acid 3(-yl) sebacate prepolymer (PreLCA) was obtained with a yield of 50%.

Workup

  1. customThe solvent was partially removed
  2. customto crystallize at -10° C
  3. filtrationThe product was filtered out
  4. washwashed with a small amount of cold acetic anhydride
  5. customdried under vacuum at room temperature for two days

Sources & evidence

ORD record
ord-796cbf678a554efea7d9dda6f7169654
Source dataset
uspto-grants-1999_09
Patent number
US05955068

Linked notes

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