Acetic Acid → Biotin

HRID 2057130Notes

Reaction equation

HRID 2057130 reaction equation
C1(C)C=C(C)C=C(C)C=1.CS(O)(=O)=O.C([CH:22]([CH2:26][CH2:27][CH2:28][C@H:29]1[C@@H:37]2[C@@H:32]([NH:33][C:34]([NH:36]2)=[O:35])[CH2:31][S:30]1)[C:23](=[O:25])[OH:24])C1C=CC=CC=1.C(O)(=O)C>O>[OH:25][C:23]([CH2:22][CH2:26][CH2:27][CH2:28][C@H:29]1[C@@H:37]2[C@@H:32]([NH:33][C:34]([NH:36]2)=[O:35])[CH2:31][S:30]1)=[O:24]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6395Methanesulfonic Acid2×HCID 7947MesityleneHCID 18599078HCID 18599078, compound

Product 1

HCID 171548Biotin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

35.34 g of the compound obtained in Example 5, 121 ml of mesitylene and 116.1 g of methanesulfonic acid were heated at an inner temperature of 130° C. By setting a reaction starting time when the mixture reached to 125° C., the mixture was stirred at 128° C. to 133° C. for 4 hours, disappearance of monobenzylbiotin was confirmed by high performance liquid chromatography. The reaction mixture was cooled to 80° C., 30 ml of acetic acid was added thereto, and methanesulfonic acid layer was added dropwise to 710 ml of purified water. The mesitylene layer was separated, ice-cooled for 1 hour, and then, crude crystal was collected by filtration, and washed with 200 ml of water, and then, with methanol until black color of the washed solution disappeared. The crystal was dried at 50° C. by blowing air overnight to give 15.89 g of crude (+)-biotin.

Workup

  1. customreached to 125° C.
  2. customThe mesitylene layer was separated
  3. temperatureice-cooled for 1 hour
  4. filtrationcrude crystal was collected by filtration
  5. washwashed with 200 ml of water
  6. customThe crystal was dried at 50° C.
  7. customair overnight

Sources & evidence

ORD record
ord-897f3a127116482386999f2cd49282de
Source dataset
uspto-grants-2008_02
Patent number
US07335778B2

Reaction notes

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