4-Methylmorpholine → Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	Isobutyl chloroformate	HCID 62365	—
Reactant	Sodium borohydride	HCID 4311764	—
Reactant	(2R)-6-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)hexanoic acid	HCID 13585941	—
Solvent	Water	HCID 962	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	Tert-butyl n-((5r)-5-(((9h-fluoren-9-ylmethoxy)carbonyl)amino)-6-hydroxyhexyl)carbamate	HCID 11655404	—

Reaction Conditions

Temperature	-5 °C

Reaction Steps

A solution of Fmoc-D-Lys(BOC)-OH (2.102 g, 4.5 mmol) in DME (5 mL) at −15° C. was treated successively with N-methylmorpholine (0.56 mL, 5.0 mmol) and isobutyl chloroformate (0.7 mL, 5 mmol), stirred for 2 minutes, and filtered. The filter cake was washed with DME (3×5 mL) and the combined filtrate and washings were cooled to −5° C. and treated with NaBH4 (0.3 g, 7.5 mmol) in water (5 mL) and additional water (250 mL) immediately afterwards. The mixture was stirred for 15 minutes and filtered. The filter cake was washed with water and dried to provide the desired product. MS (APCI) m/e 455 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07754886B2
Source dataset	uspto-grants-2010_07
ORD ID	ord-290cb8c61e834c27bf0520d9dcd562c0
Source note	uspto-grants-2010_07