Sodium Bicarbonate → Sodium 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylate

HRID 2049173Notes

Reaction equation

HRID 2049173 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:49])[C:19]([C:24]3[N:25]=[C:26]([NH:29][C:30]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[S:27][CH:28]=3)=[N:20][O:21][CH:22]=[CH2:23])[C:15](=[O:50])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+:55]>CC(C)=O.O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:49])[C:19]([C:24]3[N:25]=[C:26]([NH:29][C:30]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[S:27][CH:28]=3)=[N:20][O:21][CH:22]=[CH2:23])[C:15](=[O:50])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=[O:3])[CH3:2].[Na+:55]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 1317117333-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Product 1

HCID 131711732Sodium 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

2.628 g of the product of Example 34 in resin form were dissolved at room temperature in 5.2 ml of acetone and 10.4 ml of a molar solution of sodium bicarbonate in water were added thereto all at once. The mixture stood at 20° C. for 1 hour and was then vacuum filtered. The recovered precipitate was rinsed twice with 2 ml of a 1-1 water-acetone mixture and with 2 ml of distilled water and was dried at 40° C. under reduced pressure to obtain 1.612 g of the syn isomer of raw sodium 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-vinyloxyimino-acetamido]-ceph-3-eme-4-carboxylate.

Workup

  1. filtrationvacuum filtered
  2. washThe recovered precipitate was rinsed twice with 2 ml of a 1-1 water-acetone mixture and with 2 ml of distilled water
  3. customwas dried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-6df77c4ffe22457f98b7fbb1af373809
Source dataset
uspto-grants-1980_04
Patent number
US04196205

Reaction notes

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