Sodium Bicarbonate → HCID 141546031, compound

HRID 2231603Notes

Reaction equation

HRID 2231603 reaction equation
[NH2:1][C@H:2]1[C@@H:5]([CH2:6][NH:7][C:8]([NH2:10])=[O:9])[NH:4][C:3]1=[O:11].C(=O)(O)[O-].[Na+].Cl.[Cl:18][CH2:19][C:20]([NH:22][C:23]1[S:24][CH:25]=[C:26](/[C:28](=[N:32]/[O:33][C:34]([CH3:49])([C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[CH3:35])/[C:29](Cl)=[O:30])[N:27]=1)=[O:21]>O.O1CCCC1>[Cl:18][CH2:19][C:20]([NH:22][C:23]1[S:24][CH:25]=[C:26](/[C:28](=[N:32]/[O:33][C:34]([CH3:49])([C:36]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=2)=[O:37])[CH3:35])/[C:29]([NH:1][C@H:2]2[C@@H:5]([CH2:6][NH:7][C:8]([NH2:10])=[O:9])[NH:4][C:3]2=[O:11])=[O:30])[N:27]=1)=[O:21]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 22166461HCID 22166461, compoundHCID 70418540HCID 70418540, compound

Product 1

HCID 141546031HCID 141546031, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 350 mg portion of the thus-obtained cis-3-amino-4-ureidomethyl-2-azetidinone (433 mg) is dissolved in a mixture of 25 ml of water and 25 ml of tetrahydrofuran and, under ice-cooling and stirring, 628 mg of sodium bicarbonate is added. Then, 1.43 g of 2-(2-chloroacetamido-4-thiazolyl)-2-(Z)-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethoxyimino]acetyl chloride hydrochloride is added and the mixture is stirred at room temperature for 2 hours. The tetrahydrofuran is distilled off under reduced pressure, 50 ml of water is added to the residue, and the mixture is stirred. The crystalline precipitate is collected by filtration, washed with aqueous sodium bicarbonate, water and hexane in that order, and dried to give 1.1 g of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-(Z)-[1-methyl-1-(p-nitrobenzyloxycarbonyl)ethoxyimino]acetamido]-4-ureidomethyl-2-azetidinone as colorless crystals.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at room temperature for 2 hours
  3. distillationThe tetrahydrofuran is distilled off under reduced pressure, 50 ml of water
  4. additionis added to the residue
  5. stirringthe mixture is stirred
  6. filtrationThe crystalline precipitate is collected by filtration
  7. washwashed with aqueous sodium bicarbonate, water and hexane in that order
  8. customdried

Sources & evidence

ORD record
ord-1df409593bf34b3494b8875bfc67206e
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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