Biotin → HCID 86643046, compound

HRID 570864Notes

Reaction equation

HRID 570864 reaction equation
[O:1]=[C:2]1[O:8][C@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[C:5]([OH:6])=[C:3]1[OH:4].[OH:13][C:14]([CH2:16][CH2:17][CH2:18][CH2:19][C@H:20]1[C@@H:28]2[C@@H:23]([NH:24][C:25]([NH:27]2)=[O:26])[CH2:22][S:21]1)=O>CC(C)=O>[O:26]=[C:25]1[NH:27][C@@H:28]2[C@H:20]([CH2:19][CH2:18][CH2:17][CH2:16][C:14]([O:12][CH2:11][C@H:9]([C@@H:7]3[C:5]([OH:6])=[C:3]([OH:4])[C:2](=[O:1])[O:8]3)[OH:10])=[O:13])[S:21][CH2:22][C@@H:23]2[NH:24]1

Participants

4

Reactant 2

HCID 171548BiotinHCID 54670067L-Ascorbic Acid

Product 1

HCID 86643046HCID 86643046, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

54.1 g of ascorbic acid (306.9 mmol; 5 eq.) and 15 g of biotin (61.4 mmol; 1 eq.) are dissolved in 180 ml of anhydrous acetone under a protective gas, 1 g of lipase (Candida antarctica) is added, and the mixture is shaken at 40° C. for 32 h. The enzyme is filtered off, 50 ml of water are added to the solution, and the product is precipitated by pouring into toluene.

Workup

  1. additionis added
  2. filtrationThe enzyme is filtered off
  3. addition50 ml of water are added to the solution
  4. customthe product is precipitated
  5. additionby pouring into toluene

Sources & evidence

ORD record
ord-84564adf4ff94a579cea84573be6e43e
Source dataset
uspto-grants-2015_05
Patent number
US09023889B2

Reaction notes

Loading…