176851-43-7

Basic information

• Product Name: N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid
• Synonyms: N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid
• CAS NO: 176851-43-7
• Molecular Weight: 354.403
• Mol File: 176851-43-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid(176851-43-7)
• EPA Substance Registry System: N-(2-(2,5-Dimethoxyphenyl)-2-hydroxyethyl)-2-((1,1-dimethylethoxy)carbonylamino)essigsaeureamid(176851-43-7)

Safety Data

• Hazardous Substances Data: 176851-43-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 133163-28-7 midodrine hydrochloride 
• 4530-20-5 BOC-glycine 
• 60407-53-6 1-(2',5'-dimethoxyphenyl)-2-aminoethanol hydrochloride 
• 3600-87-1 desglymidodrine 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 

Downstream Products

• 177018-39-2 {[(S)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 177018-40-5 {[(R)-2-(2,5-Dimethoxy-phenyl)-2-((1R,2R,4S,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 42794-76-3 midodrine 
• 133163-28-7 (R)-2-Amino-N-<2-(2,5-dimethoxyphenyl)-2-hydroxyethyl>-acetamid-hydrochlorid 
• 133163-28-7 (S)-2-Amino-N-<2-(2,5-dimethoxyphenyl)-2-hydroxyethyl>-acetamid-hydrochlorid 

Relevant articles and documents

Amidation of esters with amino alcohols using organobase catalysis

A catalytic protocol for the base-mediated amidation of unactivated esters with amino alcohol derivatives is reported. Investigations into mechanistic aspects of the process indicate that the reaction involves an initial transesterification, followed by an intramolecular rearrangement. The reaction is highly general in nature and can be extended to include the synthesis of oxazolidinone systems through use of dimethyl carbonate.

Transport characteristics of a novel peptide transporter 1 substrate, antihypotensive drug midodrine, and its amino acid derivatives

Midodrine is an oral drug for orthostatic hypotension. This drug is almost completely absorbed after oral administration and converted into its active form, 1-(2′,5′-dimethoxyphenyl)-2-aminoethanol) (DMAE), by the cleavage of a glycine residue. The intestinal H+-coupled peptide transporter 1 (PEPT1) transports various peptide-like drugs and has been used as a target molecule for improving the intestinal absorption of poorly absorbed drugs through amino acid modifications. Because midodrine meets these requirements, we examined whether midodrine can be a substrate for PEPT1. The uptake of midodrine, but not DMAE, was markedly increased in PEPT1-expressing oocytes compared with water-injected oocytes. Midodrine uptake by Caco-2 cells was saturable and was inhibited by various PEPT1 substrates. Midodrine absorption from the rat intestine was very rapid and was significantly inhibited by the high-affinity PEPT1 substrate cyclacillin, assessed by the alteration of the area under the blood concentration-time curve for 30 min and the maximal concentration. Some amino acid derivatives of DMAE were transported by PEPT1, and their transport was dependent on the amino acids modified. In contrast to neutral substrates, cationic midodrine was taken up extensively at alkaline pH, and this pH profile was reproduced by a 14-state model of PEPT1, which we recently reported. These findings indicate that PEPT1 can transport midodrine and contributes to the high bioavailability of this drug and that Gly modification of DMAE is desirable for a prodrug of DMAE. Copyright

A Separation Procedure for the Preparation of Enantiomerically Pure Midodrine

Racemic midodrine chlorohydrate (rac-1) was N-protected to yield the racemic products rac-2a-c. These were converted into the diastereomeric O-acetals 3a-c/4a-c, which can easily be separated by chromatography. After removal of the N- and O-protective gro