Phosphate → HCID 86733383, compound

HRID 1075980Notes

Reaction equation

HRID 1075980 reaction equation
[C:1]([OH:4])(=[S:3])[CH3:2].P([O-])([O-])([O-])=O.Br[CH2:11][C:12]1([CH3:38])[CH:16]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:15]2[C:25](=[O:37])[CH:26]([NH:27][C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:14]2[S:13]1>CC(C)=O>[C:1]([S:3][CH2:11][C:12]1([CH3:38])[CH:16]([C:17]([O:19][CH2:20][C:21]([Cl:22])([Cl:23])[Cl:24])=[O:18])[N:15]2[C:25](=[O:37])[CH:26]([NH:27][C:28](=[O:36])[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:14]2[S:13]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 128952622,2,2-Trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylateHCID 178418634HCID 178418634, compound

Product 1

HCID 86733383HCID 86733383, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Acetone (20 ml) and thioacetic acid (0.12 g) were added to pH 6.7 phosphate buffer (20 ml). To a mixture was added 2,2,2-trichloroethyl 2-bromomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.54 g) under stirring. After stirring for 5 hours at room temperature, the reaction mixture was post-treated in the similar manner as described in Example 6 to give oily 2,2,2-trichloroethyl 2-acetylthiomethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (0.173 g). Infrared Absorption Spectrum (CH Cl3) 3390, 1790, 1965, 1690 ~ 1685 cm-1.

Workup

  1. stirringAfter stirring for 5 hours at room temperature
  2. additionthe reaction mixture was post-treated in the similar manner

Sources & evidence

ORD record
ord-ff8c411770d54fccb24ed23c871de475
Source dataset
uspto-grants-1976_05
Patent number
US03954732

Reaction notes

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