(Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid

Name: (Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid
Brand: ChemScene
Availability: InStock
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CAS No. 80544-17-8
Cat. No. CS-0188441
Molecule weightNone
Purity≥97%
MDL No.MFCD07782100

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(Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid|CS-0188441

Structure of 80544-17-8

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General Information

CAS No. 80544-17-8
Cat. No. CS-0188441
Purity ≥97%
MDL No. MFCD07782100
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₉N₃O₅S
Molecular Weight None
Synonym(s) 2-Methoxycarbonylmethoxyimino-2-(2-aminothiazole-4-yl)ace-tie acid
SMILES C(=N\OCC(OC)=O)(\C(O)=O)/C1=CSC(N)=N1

Description

(Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid features a conjugated imino ether linkage flanked by a thiazole amine and ester-functionalized side chain, enabling direct incorporation into peptidomimetic scaffolds. This stabilized enolizable system delivers enhanced solubility in aqueous-organic mixtures while maintaining configurational integrity under standard bench conditions.

Application

(Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid serves as a key building block in the synthesis of thiazole-containing β-lactam analogs and peptidomimetics. Its constrained (Z)-configured imino ester moiety enables efficient coupling with nucleophiles under mild conditions, while the pendant aminothiazole and methoxycarbonyl groups offer orthogonal reactivity for sequential functionalization. The compound exhibits excellent bench stability and facilitates purification via standard chromatographic methods, supporting scalable applications in medicinal chemistry and API development.

Synthesis

Route1
- 17356-08-0
- 84080-70-6
- ~%
- In-stock
  
  80544-17-8
References
- WO2006/103686 A1, ; Page/Page column 9 ;

Safety Information

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GHS Pictogram :	GHS No : GHS02
Signal Word : Danger	UN#: 1325
Class : 4.1	Packing Group : Ⅲ
Hazard Statements : H228
Precautionary Statements : P210-P240-P241-P280-P370+P378

Quality Control

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Computational Chemistry Data

TPSA 124.1
LogP -0.2964
H_Acceptors 8
H_Donors 2
Rotatable_Bonds 5

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Oxime

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Thiazole compounds

Key Words

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(Z)-2-(Methoxycarbonylmethoxyimino)-2-(2-aminothiazol-4-yl)acetic acid

CAS No. 80544-17-8

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