4-Methylmorpholine → methyl N-[(2S,3S)-1-[[(2S,3S)-3-hydroxy-4-[[[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]amino]-[[4-(1,3-thiazol-2-yl)phenyl]methyl]amino]-1-phenylbutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	O-(2-Oxo-1(2H)-pyridyl)-N,N,N',N'-tetramethyluronium Tetrafluoroborate	HCID 2733204	—
Reactant	(2S)-2-((methoxycarbonyl)amino)-3-methylbutanoic acid	HCID 10942966	—
Reactant	1-[4-(Thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane	HCID 66578170	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Tetrahydrofurane dichloromethane	HCID 21919333	—
Product	methyl N-[(2S,3S)-1-[[(2S,3S)-3-hydroxy-4-[[[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]amino]-[[4-(1,3-thiazol-2-yl)phenyl]methyl]amino]-1-phenylbutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate	HCID 467968	—

Reaction Steps

Under an argon atmosphere, 321 mg (0.60 mmol) of 1-[4-(thiazol-2-yl)-phenyl]-4(S)-hydroxy-2-amino-5(S)-N-(N-methoxycarbonyl-(L)-iso-leucyl)amino-6-phenyl-2-azahexane (Example 21b) and 182 mg (1.8 mmol) of NMM in 5.8 ml of DMF are added to 126 mg (0.72 mmol) of N-methoxycarbonyl-(L)-valine and 178 mg (0.60 mmol) of TPTU in 3 ml of DMF; the mixture is stirred at room temperature for 15 hours and worked up analogously to Example 3. TLC: Rf=0.15 (methylene chloride/THF 4:1); HPLC20-100: tRet=14.5; FAB MS (M+H)+=697.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06300519B1
Source dataset	uspto-grants-2001_10
ORD ID	ord-11261abfa2024092a55d505d66b66827
Source note	uspto-grants-2001_10