Propylene Glycol → Amoxycillin 1,2-propanediolate

HRID 618632

Reaction equation

HRID 618632 reaction equation
[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:21])[C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].[CH2:26]([OH:30])[CH:27]([OH:29])[CH3:28]>ClCCl>[CH3:1][C:2]1([CH3:25])[S:6][C@@H:5]2[C@H:7]([NH:10][C:11]([C@H:13]([NH2:21])[C:14]3[CH:15]=[CH:16][C:17]([OH:20])=[CH:18][CH:19]=3)=[O:12])[C:8](=[O:9])[N:4]2[C@H:3]1[C:22]([OH:24])=[O:23].[CH2:26]([O-:30])[CH:27]([O-:29])[CH3:28]

Participants

4

Reactant 2

HCID 1030Propylene GlycolHCID 33613Amoxicillin

Product 1

HCID 131721380Amoxycillin 1,2-propanediolate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (63 ml; methanol-free) was added to amoxycillin trihydrate (3.5 g; purity by HPLC 86%; water 12.9%) with stirring at room temperature and, then, followed by the addition of 1,2-propanediol (22 ml). The reaction mixture was further stirred for about 20 min at the same temperature. The product was filtered and, then, washed on the filter with dichloromethane (100 ml). Thereafter, the product was suspended in dichloromethane (80 ml) and stirred for about 20 min at room temperature. The resulting suspension was filtered, washed on the filter with dichloromethane (100 ml) and, then, dried under vacuum overnight.

Workup

  1. stirringThe reaction mixture was further stirred for about 20 min at the same temperature
  2. filtrationThe product was filtered
  3. washwashed on the
  4. filtrationfilter with dichloromethane (100 ml)
  5. stirringstirred for about 20 min at room temperature
  6. filtrationThe resulting suspension was filtered
  7. washwashed on the
  8. filtrationfilter with dichloromethane (100 ml)
  9. customdried under vacuum overnight

Sources & evidence

ORD record
ord-e1185c721c3746e6995ee74ddb9cb0c1
Source dataset
uspto-grants-1999_09
Patent number
US05955458

Linked notes

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