Toluene → Lovastatin phenylboronate

HRID 381712

Reaction equation

HRID 381712 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[C:30]1([B:36]([OH:38])[OH:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(C)C=CC=CC=1>O>[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[C:30]1([B:36]([O-:38])[O-:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 53232LovastatinHCID 66827Phenylboronic Acid

Product 1

HCID 86757523Lovastatin phenylboronateYield 94,323.398%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A suspension of lovastatin (350 g, 0.865 mmol), phenylboronic acid (110.8 g, 0.909 mmol) and toluene (1.75 L) was heated with agitation under a nitrogen atmosphere. A reflux temperature of 100-105° C. was maintained for 55 minutes as water was collected and separated from the reaction mixture. The solution was cooled and 1.39 L of toluene was removed by vacuum distillation at 40-50° C. The concentrated solution was treated with hexanes (3.15 L) between 40-50° C. The resulting suspension was cooled to 0-5° C. for 2 hours and the product was filtered and washed with 0-5° C. hexanes (350 mL). The product was dried at 35-40° C. under vacuum to provide 427.9 g (37%) of lovastatin phenylboronate at >99% purity by HPLC.

Workup

  1. temperaturewas heated with agitation under a nitrogen atmosphere
  2. customwas collected
  3. customseparated from the reaction mixture
  4. temperatureThe solution was cooled
  5. custom1.39 L of toluene was removed by vacuum distillation at 40-50° C
  6. additionThe concentrated solution was treated with hexanes (3.15 L) between 40-50° C
  7. filtrationthe product was filtered
  8. washwashed with 0-5° C. hexanes (350 mL)
  9. customThe product was dried at 35-40° C. under vacuum

Sources & evidence

ORD record
ord-5e1f10e0eb304c878b22faec6b0fa8b2
Source dataset
uspto-grants-2001_10
Patent number
US06307066B1

Linked notes

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