7099-77-6

Basic information

• Product Name: Acetamide, N-(hydroxymethyl)-N-methyl-
• Synonyms: N-methyl-N-hydroxymethylacetamide;N-Methyl-N-hydroxymethyl-acetamid;dimethylformamide-methanol;N-Hydroxymethyl-N-methyl-acetamide
• CAS NO: 7099-77-6
• Molecular Formula: C4H9NO2
• Molecular Weight: 103.121
• Mol File: 7099-77-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 203.5±23.0 °C(Predicted)
• Density: 1.069±0.06 g/cm3(Predicted)
• CAS DataBase Reference: Acetamide, N-(hydroxymethyl)-N-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, N-(hydroxymethyl)-N-methyl-(7099-77-6)
• EPA Substance Registry System: Acetamide, N-(hydroxymethyl)-N-methyl-(7099-77-6)

Safety Data

• Hazardous Substances Data: 7099-77-6(Hazardous Substances Data)

Upstream product

• 51164-31-9 (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid (acetyl-methyl-amino)-methyl ester 

Relevant articles and documents

Acyloxymethyl as a drug protecting group. Part 3. Tertiary O-amidomethyl esters of penicillin G: Chemical hydrolysis and anti-bacterial activity

Purpose. O-(N-alkylamido)methyl esters of penicillin G were studied as a new class of prodrugs. Methods. Their hydrolysis in aqueous buffers containing 20% (v/v) of acetonitrile was investigated by HPLC. Results. A U-shaped pH-rate profile was seen with a pH-independent process extending from pH ca. 2 to pH ca. 10. This pathway is characterised by kinetic data that are consistent with a unimolecular mechanism involving rate-limiting iminium ion formation and penicillinoate expulsion. Penicillin G and the corresponding amide are the ultimate products detected and isolated, indicating that p-lactam ring opening is much slower than ester hydrolysis. The O-(N-alkylamido)methyl esters of penicillin G displayed similar in vitro antibacterial activity to penicillin G itself. Conclusions. Compared to the penicillin G derivatives, the much higher stability of the O-(N-methylbenzamido)methyl benzoate, acetate and valproate esters (which gave rise to a Bronsted β(1g) value of ca. -1) suggests that tertiary N-acyloxymethylamides may be useful prodrugs for carboxylic acid drugs with pK(a) > 4.