Hydrochloric Acid → HCID 13362788, compound

HRID 1164566Notes

Reaction equation

HRID 1164566 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].C(=O)(O)[O-].[Na+].Br[CH2:11][C:12]([CH2:14][C:15]([NH:17][CH:18]1[C:28](=[O:29])[N:20]2[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH2:23][S:24][C@H:19]12)=[O:16])=O.Cl>O1CCCC1.O>[NH2:1][C:2]1[S:3][CH:11]=[C:12]([CH2:14][C:15]([NH:17][CH:18]2[C:28](=[O:29])[N:20]3[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH2:23][S:24][C@H:19]23)=[O:16])[N:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 886081427-[2-(2-Bromoacetyl)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 13362788HCID 13362788, compoundYield 51.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Thiourea (663 mg), sodium bicarbonate (732 mg) and water (20 ml) were added to a stirred solution of 7-[2-(2-bromoacetyl)acetamido]-3-cephem-4-carboxylic acid (2.11 g) in tetrahydrofuran (20 ml) under ice-cooling and stirred at the same temperature for an hour. After the resultant solution was adjusted to pH 4.0 with dilute hydrochloric acid, the precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-amino-4-thiazolyl)acetamido]-3-cephem-4-carboxylic acid (1.01 g).

Workup

  1. temperaturecooling
  2. filtrationthe precipitates were collected by filtration
  3. washwashed with water
  4. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-079cc1325b154269bc1cf0c537636379
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

Loading…