2-Dimethylaminopyridine → HCID 86704073, compound

https://huagongshe.com/reaction/2206382

Participants

Role	Name	HCID	Charge
Reactant	2-Dimethylaminopyridine	HCID 21885	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-N-Boc-aminopropionic acid	HCID 268471	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 72550676	HCID 72550676	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86704073	HCID 86704073	90%

Reaction Steps

In a manner similar to the method described in Example 3, chiral 2-hydroxyethyl 4-((2R,3S,4R,5S)-3-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-fluorophenyl)-4-cyano-5-neopentylpyrrolidine-2-carboxamido)-3-methoxybenzoate (Example 1, 105.2 mg, 0.159 mmol) was reacted with (R)-(2-(tert-butoxycarbonylamino)propanoic acid (Chem-Impex, 75 mg, 0.398 mmol), HATU (Bachem, 151 mg, 0398 mmol), N,N-diisopropylethylamine (104 mg, 0.14 mL, 0.802 mmol) and dimethylaminopyridine (Aldrich, 10.8 mg, 0.088 mmol) in dimethyl formamide (8 mL) to give chiral 4-{[(2R,3S,4R,5S)-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-amino}-3-methoxy-benzoic acid 2-((R)-2-tert-butoxycarbonylamino-propionyloxy)-ethyl ester as a white solid (119 mg, 89% yield). MS (ES+) m/z calcd. for C41H47Cl2F2N4O8 [(M+H)+]: 831. found: 831.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09371280B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-e79d5080e3af4e1b8138a5f62e1758dc
Source note	uspto-grants-2016_06