Diisopropylethylamine → N-[N-(2-Heptenoyl)-3,5-difluoro-L-phenylalanyl]cyclo(Ser*-Pro-L-Pip-Ala-4beta-methyl-Pro-)

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Heptenoic acid	HCID 5282709	—
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	(S)-2-(3,5-Difluorophenyl)-1-((3S,9S,13S,15R,19S,22S)-15, 19-Dimethyl-2,8,12,18,21-pentaoxo-11-oxa-1,7,17,20-tetraaza-tetracyclo[20.4.0.03,7.013,17]hexacos-9-ylcarbamoyl)-ethylammonium 2,2,2-trifluoroacetate	HCID 86598033	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Acetonitrile--water (1/1)	HCID 18373917	—
Product	N-[N-(2-Heptenoyl)-3,5-difluoro-L-phenylalanyl]cyclo(Ser*-Pro-L-Pip-Ala-4beta-methyl-Pro-)	HCID 11679386	—

Reaction Steps

101.5 mg (0.13 mmol) of the compound from example 29A and 23.0 mg (0.17 mmol) of trans-2-heptenoic acid are introduced under argon into anhydrous dimethylformamide (2 ml) at 0° C. and then 65.0 mg (0.17 mmol) of HATU and 0.025 ml (0.14 mmol) of ethyldiisopropylamine are added. After 30 min, a further 0.05 ml (0.29 mmol) of ethyldiisopropylamine are added to the reaction mixture. The reaction mixture is stirred overnight with slow warming to RT. The reaction solution is subjected directly to an RP-HPLC using acetonitrile/water as eluent. In the course of this, 63 mg (62% of th.) of a colorless solid are obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07405201B2
Source dataset	uspto-grants-2008_07
ORD ID	ord-7124a5e3e5414e6c9a84f8113aefb998
Source note	uspto-grants-2008_07