Glycolic Acid → 2-hydroxy-N-(2-hydroxy-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Glycolic Acid	HCID 757	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	1-Amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethylphenoxy}-propan-2-ol	HCID 59497883	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-hydroxy-N-(2-hydroxy-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide	HCID 23729248	1.7%

Reaction Steps

To a solution of crude 1-amino-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl phenoxy}-propan-2-ol (0.22 mmol) in DMF (1 mL) are added glycolic acid (25 mg), DIPEA (0.1 mL) and finally TBTU (60 mg). The mixture is stirred for 15 h at rt, evaporated and the residue purified by TLC (SiO2, EA) to give 2-hydroxy-N-(2-hydroxy-3-{4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,3,4]oxadiazol-2-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide (1.8 mg); LC-MS: tR=0.97 min, [M+1]+=474.26.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08003800B2
Source dataset	uspto-grants-2011_08
ORD ID	ord-8cc3ecf1a3284daf829322fe9b88a584
Source note	uspto-grants-2011_08