Ammonium Hydroxide → Levobupivacaine

HRID 643763Notes

Reaction equation

HRID 643763 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.C(C(C(C([O-])=O)O)O)([O-])=O.[OH-].[NH4+]>O>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86591002Levobupivacaine tartrate

Product 1

HCID 92253Levobupivacaine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

45 g of levobupivacaine tartrate were dissolved in 222 mL of water under stirring. Concentrated ammonium hydroxide was added under stirring until the pH adjusted at 9-10. The solids were filtered and washed with 222 mL of water. The solids were dried in an oven with temperature around 45° C. until constant weight. Yield 27.6 g of enriched levobupivacaine free base (70%≦ee≦80%), MP=125-132° C.

Workup

  1. stirringunder stirring until the pH
  2. filtrationThe solids were filtered
  3. washwashed with 222 mL of water
  4. customThe solids were dried in an oven with temperature around 45° C. until constant weight

Sources & evidence

ORD record
ord-73b4d2ebe2184472a1829a8c3c010dc1
Source dataset
uspto-grants-2010_04
Patent number
US07700629B2

Reaction notes

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