Trifluoroacetic acid → (S)-N-(4-Iodo-phenyl)-2-[(R)-4-(4-methoxy-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionamide

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	Triethylamine	HCID 8471	—
Reactant	L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-	HCID 77857	—
Reactant	O-benzotriazol-1-yl-tetramethyluronium	HCID 130500	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	HCID 28976652	HCID 28976652	—
Reactant	(R)-tert-Butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid	HCID 67001404	—
Product	(S)-N-(4-Iodo-phenyl)-2-[(R)-4-(4-methoxy-phenyl)-2,5-dioxo-imidazolidin-1-yl]-3-phenyl-propionamide	HCID 57935156	—

Reaction Steps

Prepared by the same method as described in example 1 except that (i) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 1, (ii) 4-iodoaniline was used in place of 4-bromoaniline in step 2, and (iii) the trifluoroacetic acid salt of (S)-2-amino-N-(4-iodo-phenyl)-3-phenyl-propionamide was isolated in step 3 and used directly in step 4 with 1.0 equivalent of triethylamine and (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride as the coupling reagent in place of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexaflurorophosphate.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07612212B2
Source dataset	uspto-grants-2009_11
ORD ID	ord-651c6c2b9fe645caac3a281726f7d2f4
Source note	uspto-grants-2009_11