Chlorosuccinimide → (R)-tert-Butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid

https://huagongshe.com/reaction/561989

Participants

Role	Name	HCID	Charge
Reactant	Chlorosuccinimide	HCID 31398	—
Reactant	2-Bromoethyl methyl ether	HCID 80972	—
Reactant	3-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acid	HCID 57771978	—
Reactant	(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid	HCID 66815126	—
Reactant	(R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid	HCID 66815165	—
Reactant	{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester	HCID 67001749	—
Product	(R)-tert-Butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid	HCID 66815175	—

Reaction Steps

Prepared by the same method as described in example 1 except that (i) (2S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 53-E; (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 53-F was omitted and (iii) (R)-tert-butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid was in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 53-G. (R)-tert-Butoxycarbonylamino-[4-(2-methoxy-ethoxy)-phenyl]-acetic acid was prepared as described in example 1 for the preparation of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid except that 1-bromo-2-methoxy-ethane was used in place of 2-(2-iodo-ethoxy)-2-methyl-propane. HR-MS: calcd for C29H26FlN4O4 [M+H+] 641.1056. Found 641.1053.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08063085B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-8130d420164a4c10ba512b26bc0c39c0
Source note	uspto-grants-2011_11