Hydrochloric Acid → 64221-86-9

HRID 224412Notes

Reaction equation

HRID 224412 reaction equation
[CH3:1][C@@H:2]([OH:18])[C@H:3]1[C:9](=[O:10])[N:8]2[C@@H:4]1[CH2:5][C:6]([S:14][CH2:15][CH2:16][NH2:17])=[C:7]2[C:11]([OH:13])=[O:12].[OH-].[Na+].Cl.[CH:22](=[NH:25])OC.Cl>P([O-])([O-])([O-])=O>[CH3:1][C@@H:2]([OH:18])[C@H:3]1[C:9](=[O:10])[N:8]2[C@@H:4]1[CH2:5][C:6]([S:14][CH2:15][CH2:16][N:17]=[CH:22][NH2:25])=[C:7]2[C:11]([OH:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 441128(+)-ThienamycinHCID 12657462Methyl methanimidate--hydrogen chloride (1/1)

Product 1

HCID 10483864221-86-9

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

Thienamycin (517 mg) is dissolved in pH 7 0.1 N phosphate buffer (25 ml) and cooled in an ice bath with magnetic stirring. The solution is adjusted to pH 8.5 using 2.5 N sodium hydroxide solution dispensed from an automatic burette. While maintaining a pH of 8.5, methyl formimidate hydrochloride (711 mg) is added portionwise over a 2-3 minutes. After an additional 10 minutes, the pH of the solution is brought to 7.0 using 2.5 N hydrochloric acid. The solution is chromatographed on a column of XAD-2 resin (150 cc) which is eluted with water. The N-formimidoyl Thienamycin derivative elutes in 1.5-2.0 column volumes (200-300 cc) and is lyophilized to a white solid (217 mg). UV (pH 7 0.1 N phosphate buffer)λmax 297 nm (8,590). ir (Nujol mull) 1767 cm-1 (β-lactam) nmr (D2O)δ1.37 (d, J=6 Hz, CH3 --CH), 3.0-3.75 (m, --CH2 --), 4.2-4.8 (m, C5H, C6H, C7H), 7.86 ##STR76##

Workup

  1. temperaturecooled in an ice bath with magnetic stirring
  2. additionis added portionwise over a 2-3 minutes
  3. customThe solution is chromatographed on a column of XAD-2 resin (150 cc) which
  4. washis eluted with water

Sources & evidence

ORD record
ord-36628d22eca54a37981c7bca9ae1f628
Source dataset
uspto-grants-1980_11
Patent number
US04232030

Reaction notes

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