2(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide → 3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide

Participants

Role	Name	HCID	Charge
Reactant	2(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide	HCID 86752114	—
Reactant	3-[N-tert-butoxy-carbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-[(2-methyl)propen-3-yl]-propionic acid (N-butyl)amide	HCID 86752115	—
Reactant	5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(R),7,7-trimethyl-8-[3(R,S)-allyloxymethyl-1,2,3,4-tetrahydroquinolin-1-ylcarbonyl]-octanoic acid (N-butyl)amide	HCID 131720529	—
Reactant	5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-2(S)-isopropyl-7,7dimethyl-8-[2(R,S)-ethylaminocarbonyl-3,4-dihydro-2H1,4-benzothiazin-4-ylcarbonyl]-octanoic acid (N-butyl)amide	HCID 131720534	—
Product	3-[N-Tert-butoxycarbonyl-4(S)-(3-carboxy-2,2-dimethylpropyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide	HCID 86752113	—

Reaction Steps

starting from 505 mg of 2(R)-benzyl-9-benzyloxy-5(S)-tert-butoxycarbonyl-amino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-methyl)amide via 3-[N-tert-butoxycarbonyl-4(S)-(4-benzyloxy-2,2-dimethylbutyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzyl-propionic acid (N-methyl)amide (Rf (A)=0.43; FAB-MS:(M+H)+ =567) and 3-[N-tert-butoxycarbonyl-4(S)-(2,2-dimethyl-4-hydroxybutyloxy-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-benzylpropionic acid (N-methyl)amide (Rf (B)=0.14; FAB-MS:(M+H)+ =477) in a manner analogous to that described in Examples 74a,74b and 74c), as the pure diastereomer: Rf (L)=0.17; FAB-MS:(M+H)+ =491.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05719141
Source dataset	uspto-grants-1998_02
ORD ID	ord-18cb69d9c74e4aa5ad578c58607c8a13
Source note	uspto-grants-1998_02