Dimethyl Sulfide → DMS bupivacaine

HRID 53078Notes

Reaction equation

HRID 53078 reaction equation
[CH3:1][S:2][CH3:3].[CH3:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:13]([C:14]([NH:16][C:17]2[C:18]([CH3:24])=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:23])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1>C(O)C>[CH3:1][S:2][CH3:3].[CH3:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:13]([C:14]([NH:16][C:17]2[C:18]([CH3:24])=[CH:19][CH:20]=[CH:21][C:22]=2[CH3:23])=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 2474Bupivacaine (USAN:INN:BAN)

Product 1

HCID 131719970DMS bupivacaine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A uniform mixture of DMS and bupivacaine was formed by combining DMS dissolved in 95% ethanol with bupivacaine dissolved in 95% ethanol. The solution was air-dried under the hood at room temperature until the ethanol evaporated and left behind a well-dispersed mixture of dry crystalline DMS and bupivacaine. The crystalline mixture was pulverized under mortar and pestle and combined with copolymer. The rest of the procedures followed those described for CHP PLAMs. All DMS/bupivacaine PLAMs were synthesized using large bore Teflon® tubing.

Workup

  1. dry with materialThe solution was air-dried under the hood at room temperature until the ethanol
  2. customevaporated
  3. waitleft behind a well-dispersed mixture of dry crystalline DMS and bupivacaine

Sources & evidence

ORD record
ord-bea38d61458940fea2cd3e1c387f5571
Source dataset
uspto-grants-1997_04
Patent number
US05618563

Reaction notes

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