Methanol → thiazol-5-ylmethyl N-[(1S,3S,4S)-1-benzyl-3-hydroxy-4-[[(2S)-3-methyl-2-[(2-morpholinothiazol-4-yl)methoxycarbonylamino]butanoyl]amino]-5-phenyl-pentyl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	thiazol-5-ylmethyl N-[(1S,2S,4S)-1-benzyl-2-hydroxy-4-[[(2S)-3-methyl-2-[(2-morpholinothiazol-4-yl)methoxycarbonylamino]butanoyl]amino]-5-phenyl-pentyl]carbamate	HCID 482932	—
Reactant	(2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane	HCID 10812314	—
Reactant	1,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamate	HCID 11101978	—
Solvent	Chloroform	HCID 6212	—
Product	thiazol-5-ylmethyl N-[(1S,3S,4S)-1-benzyl-3-hydroxy-4-[[(2S)-3-methyl-2-[(2-morpholinothiazol-4-yl)methoxycarbonylamino]butanoyl]amino]-5-phenyl-pentyl]carbamate	HCID 482933	—

Reaction Steps

Using the procedure of Example 1 U but replacing N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine with the resultant compound of Example 11 E and replacing (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane with (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane provided, after silica gel chromatography using 2% methanol in chloroform, 196 mg (90%) of the desired compound (Rf 0.19, 4% methanol in chloroform), mp. 146°-148° C. Mass spectrum: (M+H)+ =751.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05846987
Source dataset	uspto-grants-1998_12
ORD ID	ord-98592aa43b1f46568e501135070cdd33
Source note	uspto-grants-1998_12