1438852-72-2

Basic information

• Product Name: (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylic acid
• Synonyms: (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylic acid
• CAS NO: 1438852-72-2
• Molecular Weight: 233.24
• Mol File: 1438852-72-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylic acid(1438852-72-2)
• EPA Substance Registry System: (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylic acid(1438852-72-2)

Safety Data

• Hazardous Substances Data: 1438852-72-2(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1262410-84-3 ( R)-(-)-tert-butyl 3-fluoro-3-(hydroxymethyl)pyrrolidine-1-carboxylate 
• 1438852-70-0 1-tert-butyl 3-methyl (3R)-3-fluoropyrrolidine-1,3-dicarboxylate 
• 1438852-68-6 methyl (3R)-1-benzyl-3-fluoropyrrolidine-3-carboxylate 
• 1279669-60-1 methyl 1-benzyl-3-fluoropyrrolidine-3-carboxylate 
• 77-92-9 citric acid 

Downstream Products

• 1438852-77-7 methyl N-{(2R,3R)-3-[(2S)-1-{(3R,4S,5S)-4-[(N-{[(3R)-3-fluoropyrrolidin-3-yl]carbonyl}-L-valyl)(methyl)amino]-3-methoxy-5-methylheptanoyl}pyrrolidin-2-yl]-3-methoxy-2-methylpropanoyl}-L-phenylalaninate, trifluoroacetic acid salt 
• 1438852-74-4 lithium (3R)-1-(tert-butoxycarbonyl)-3-fluoropyrrolidine-3-carboxylate 
• 1601461-40-8 tert-butyl (3R)-3-fluoro-3-([((1R)-1-phenylethyl)amino]carbonyl)pyrrolidine-1-carboxylate 
• 1262410-84-3 ( R)-(-)-tert-butyl 3-fluoro-3-(hydroxymethyl)pyrrolidine-1-carboxylate 

Relevant articles and documents

Determination of the absolute configuration of (+)- and (?)-N-CBZ-3-fluoropyrrolidine-3-methanol using vibrational circular dichroism and confirmation of stereochemistry by conversion to (R)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate

Racemic N-CBZ-3-fluoropyrrolidine-3-methanol (±)-1 was resolved by preparative chiral HPLC. The absolute configuration of the enantiomers of 1 was identified by vibrational circular dichroism and confirmed by chemical synthesis, which involved exchanging the CBZ protecting group of (?)-1 with Boc, followed by oxidation with RuCl3, NaIO4, activation of the resulting acid with carbonyl diimidazole and reaction with (R)-α-methylbenzylamine to give (R)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl) pyrrolidine-1-carboxylate 7. The latter was compared with authentic (S)-tert-butyl 3-fluoro-3-(((R)-1-phenylethyl)carbamoyl)pyrrolidine-1-carboxylate 6 and its diastereomer 7; the configuration of diastereomer 6 was obtained by an X-ray diffraction study. This established that the enantiomer (?)-1 had an (R)-configuration.

NOVEL COMPOUNDS

A compound of formula (I): wherein R represents H or F, or a salt thereof.

CYTOTOXIC PEPTIDES AND ANTIBODY DRUG CONJUGATES THEREOF

The present invention is directed to cytotoxic pentapeptides, to antibody drug conjugates thereof, and to methods for using the same to treat cancer.