Water → Budenoside

HRID 922077Notes

Reaction equation

HRID 922077 reaction equation
O.C[CH2:3][CH2:4][CH:5]1[O:25][C@:24]2([C:26]([CH2:28][OH:29])=[O:27])[C@@H:7]([CH2:8][C@@H:9]3[C@:23]2([CH3:30])[CH2:22][C@H:21]([OH:31])[C@H:20]2[C@H:10]3[CH2:11][CH2:12][C:13]3[C@:19]2([CH3:32])[CH:18]=[CH:17][C:15](=[O:16])[CH:14]=3)[O:6]1>ClCCl>[CH3:3][CH2:4][CH:5]1[O:25][C@:24]2([C:26]([CH2:28][OH:29])=[O:27])[C@@H:7]([CH2:8][C@@H:9]3[C@:23]2([CH3:30])[CH2:22][C@H:21]([OH:31])[C@H:20]2[C@H:10]3[CH2:11][CH2:12][C:13]3[C@:19]2([CH3:32])[CH:18]=[CH:17][C:15](=[O:16])[CH:14]=3)[O:6]1

Participants

4

Reactant 2

HCID 962Water2×HCID 5281004Budesonide

Product 1

HCID 13298169Budenoside

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Water (800 mL) was charged to a 1 L stirred crystallizer fitted with a thermo-regulation jacket. The temperature was adjusted to 45° C. Water was pumped around a recirculation loop using a diaphragm pump (operating at 20 L/h) and a 250 ml thermo-regulated glass ultrasonic flow-cell fitted with a 30 mm diameter 20 kHz ultrasonic probe. The probe was held at the highest position in the flow-cell and sealed/clamped at a point of zero vibration (null point). The flow-cell was thermo-regulated at 45° C. Continuous ultrasound was applied at 15 W power, 5 micron amplitude. Budesonide (0.8 g) was dissolved in dichloromethane (80 mL). The solution was dispersed in an aqueous phase held at 45° C. consisting of 800 ml of a 0.2% (w/v) solution of Tween 80. The dichloromethane solution was pumped into the ultrasonic flow-cell using a second inlet on the underside of the flow-cell at a rate of 20 ml/h. The resulting suspension was stirred for 30 minutes at 300 rpm with sonication. Product was collected as aqueous suspension.

Workup

  1. customfitted with a thermo-regulation jacket
  2. customwas adjusted to 45° C
  3. customwas thermo-regulated at 45° C
  4. additionThe solution was dispersed in an aqueous phase
  5. customheld at 45° C.
  6. stirringThe resulting suspension was stirred for 30 minutes at 300 rpm with sonication
  7. customProduct was collected as aqueous suspension

Sources & evidence

ORD record
ord-ff49b72de4334be6b5d8695c241d3563
Source dataset
uspto-grants-2016_03
Patent number
US09278323B2

Reaction notes

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