2(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide → 3-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide

Participants

Role	Name	HCID	Charge
Reactant	2(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide	HCID 57261199	—
Reactant	3(R)-But-2-enyl-5(S)-[5-tert-butyl-diphenylsilyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran	HCID 67625916	—
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	—
Product	3-[N-tert-butoxycarbonyl-4(S)-(4-tert-butyl-diphenylsilyloxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-but-2-enyl-propionic acid (N-butyl)amide	HCID 131720537	—

Reaction Steps

Starting from 472 mg of 3(R)-but-2-enyl-5(S)-[5-tert-butyl-diphenylsilyloxy-1(S)-tert-butoxycarbonylamino-3,3-dimethyl-pentyl]-2-oxo-tetrahydrofuran via 2(R)-but-2-enyl-9-tert-butyldiphenylsilyloxy-5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7,7-dimethyl-nonanoic acid (N-butyl)amide (Rf (A)=0.64; FAB-MS: (M+H)+ =681) analogously to Examples 74b and 74c): Rf (B)=0.71; FAB-MS: (M+H)+ =721.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05719141
Source dataset	uspto-grants-1998_02
ORD ID	ord-73884d7e134f4e6fb52a6f6683734351
Source note	uspto-grants-1998_02