(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acid → HCID 88024151, compound

HRID 1459603Notes

Reaction equation

HRID 1459603 reaction equation
C(OC(OC(P(OOCC)(OOCC)=O)(P(OOCC)(OOCC)=O)CC(O)=O)=O)(C)(C)C.[C:34]([O:38][C:39]([O:41][C:42]([P:57]([O:63][O:64][CH2:65][CH3:66])([O:59][O:60][CH2:61][CH3:62])=[O:58])([P:47]([O:53][O:54][CH2:55][CH3:56])([O:49][O:50][CH2:51][CH3:52])=[O:48])[CH2:43][C:44](Cl)=[O:45])=[O:40])([CH3:37])([CH3:36])[CH3:35].[CH3:67][O:68]/[N:69]=[C:70](/[C:74]1[N:75]=[C:76]([NH2:79])[S:77][CH:78]=1)\[C:71]([OH:73])=[O:72]>N1C=CC=CC=1>[CH3:67][O:68]/[N:69]=[C:70](/[C:74]1[N:75]=[C:76]([NH:79][C:44](=[O:45])[CH2:43][C:42]([O:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])([P:57]([O:63][O:64][CH2:65][CH3:66])([O:59][O:60][CH2:61][CH3:62])=[O:58])[P:47]([O:53][O:54][CH2:55][CH3:56])([O:49][O:50][CH2:51][CH3:52])=[O:48])[S:77][CH:78]=1)\[C:71]([OH:73])=[O:72]

Participants

5

Reactant 3

HCID 5486924(alphaZ)-2-Amino-alpha-(methoxyimino)-4-thiazoleacetic acidHCID 53772307HCID 53772307, compoundHCID 54509263HCID 54509263, compound

Product 1

HCID 88024151HCID 88024151, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Hydroxy-3,3-diphosphonopropanoic acid, tetramethyl ester is converted to 3-(tert-butoxycarbonyloxy)-3,3-bis(diethoxyphosphono)propionic acid and then to 3-(tert-butoxycarbonyloxy)-3,3-bis(diethoxyphosphono)propanoyl chloride. The acid chloride is then added to α-(Z-methoxyimino)-α-(2-aminothiazol-4-yl)-acetic acid and pyridine to form α-(Z-methoxyimino)-α-{2-[3-(tert-butoxycarbonyloxy)-3,3-bis(diethoxyphosphono)-propanoyl-amino]-thiazol-4-yl}-acetic acid. The latter is reacted with oxaloyl chloride to form the acid chloride, α-(Z-methoxyimino)-α-{2-[3-(tert-butoxycarbonyloxy)-3,3-bis(diethoxyphosphono)-propanoyl-amino)-thiazol-4-yl]-acetyl chloride. This acid chloride is reacted with 7β-amino-3-acetoxymethyl-3-cephem-4-carboxylic acid and pyridine and gives 7β-{α-(Z-methoxyimino)-α-[2-(3-tert-butoxycarbonyloxy)-3,3-bis(diethoxyphosphono)propanoyl-amino)-thiazol-4-yl]-acetamido}-3-acetoxymethyl-3-cephem-4-carboxylic acid. Deprotection with trifluoroacetic acid and anisole yields the title compound.

Sources & evidence

ORD record
ord-0ef459a95d394a03a5bf2eaf2b51c84d
Source dataset
uspto-grants-1998_12
Patent number
US05854227

Reaction notes

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