Lincomycin Hydrochloride Anhydrous → Lincomycin trans-traumatate

HRID 865828

Reaction equation

HRID 865828 reaction equation
[C:1]([OH:16])(=[O:15])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[CH3:17][CH2:18][CH2:19][C@H:20]1[CH2:24][N:23]([CH3:25])[C@H:22]([C:26]([NH:28][C@H:29]([C@H:41]([OH:43])[CH3:42])[C@H:30]2[O:35][C@H:34]([S:36][CH3:37])[C@H:33]([OH:38])[C@@H:32]([OH:39])[C@H:31]2[OH:40])=[O:27])[CH2:21]1.Cl>O>[CH3:17][CH2:18][CH2:19][C@H:20]1[CH2:24][N:23]([CH3:25])[C@H:22]([C:26]([NH:28][C@H:29]([C@H:41]([OH:43])[CH3:42])[C@H:30]2[O:35][C@H:34]([S:36][CH3:37])[C@H:33]([OH:38])[C@@H:32]([OH:39])[C@H:31]2[OH:40])=[O:27])[CH2:21]1.[C:1]([O-:16])(=[O:15])/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 64710Lincomycin Hydrochloride AnhydrousHCID 5283028Traumatic Acid

Product 1

HCID 131719628Lincomycin trans-traumatate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
4 °C

Procedure

2.28 g of trans-traumatic acid (10 mmol) are suspended in 100 ml of water cooled to 4° C. A solution of 8.86 g of lincomycin hydrochloride (20 mmol) in 100 ml water is eluted through a column cooled to 4° C. containing 35 ml of [OH--] Dowex 1×8 resin. The eluate free from chlorides is collected in the form of a suspension of traumatic acid kept under continuous stirring at 4° C. The resulting solution is frozen and lyophilized. The reaction yield is 10.1 g of dry product.

Workup

  1. temperaturecooled to 4° C.
  2. additioncontaining 35 ml of [OH--] Dowex 1×8 resin
  3. customThe eluate free from chlorides is collected in the form of a suspension of traumatic acid
  4. temperatureThe resulting solution is frozen
  5. customThe reaction yield is 10.1 g of dry product

Sources & evidence

ORD record
ord-17f7361707a3461c8321adcfc153790c
Source dataset
uspto-grants-1996_10
Patent number
US05567716

Linked notes

Loading…