Diethyl Ether → 2-Methyl-7-[2-(2-aminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid hydrochloride

HRID 1701134Notes

Reaction equation

HRID 1701134 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:26])[CH:12]([NH:13][C:14](=[O:25])[C:15]([C:17]3[N:18]=[C:19]([NH:22]C=O)[S:20][CH:21]=3)=[O:16])[C@H:4]2[S:3]1.P(Cl)(Cl)([Cl:29])=O.C(OCC)C>CO>[ClH:29].[CH3:1][CH:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[N:5]2[C:11](=[O:26])[CH:12]([NH:13][C:14](=[O:25])[C:15]([C:17]3[N:18]=[C:19]([NH2:22])[S:20][CH:21]=3)=[O:16])[C@H:4]2[S:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24813Phosphorus oxychlorideHCID 1317114932-Methyl-7-[2-(2-formylaminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acidHCID 178427249HCID 178427249, compound

Product 1

HCID 1317117222-Methyl-7-[2-(2-aminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-methyl-7-[2-(2-formylaminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, which can be represented as 2-methyl-7-[2-(2-formylimino-2,3-dihydrothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid, (3.0 g.) in methanol (60 ml.) was added dropwise phosphorus oxychloride (2.55 L g.) under ice-cooling and stirring, and the mixture was stirred for 3.5 hours at the same temperature and then for 30 minutes at room temperature. After the reaction, the reaction mixture was poured into diethyl ether (400 ml.). The precipitates were collected by filtration, washed with diethyl ether and then dried to give 2-methyl-7-[2-(2-aminothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid hydrochloride, which can be represented as 2-methyl-7-[2-(2-imino-2,3-dihydrothiazol-4-yl)glyoxylamido]-3-cephem-4-carboxylic acid hydrochloride (2.2 g.), mp >270° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3.5 hours at the same temperature
  3. customAfter the reaction
  4. filtrationThe precipitates were collected by filtration
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-7e16bc96b628492c823d476f15a52e08
Source dataset
uspto-grants-1980_03
Patent number
US04191762

Reaction notes

Loading…