4-Methylmorpholine → HCID 67407303, compound

https://huagongshe.com/reaction/1949643

Participants

Role	Name	HCID	Charge
Reactant	4-Methylmorpholine	HCID 7972	—
Reactant	(S)-2-((tert)-Butoxycarbonyl)amino)butanoic acid	HCID 2755934	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	HCID 67410675	HCID 67410675	—
Solvent	Diethyl Ether	HCID 3283	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	N-methyl-2-pyrrolidone	HCID 13387	—
Product	HCID 67407303	HCID 67407303	71%

Reaction Conditions

Temperature	0 °C

Reaction Steps

To a solution containing Boc-L-Abu-OH (170 mg, 0.83 mmol) in anhydrous NMP (2 mL) was cooled to 0° C. HATU (316 mg, 0.83 mmol) and NMM (115 mg, 1.08 mmol) were added followed by the addition of crude 63 (242 mg, 0.75 mmol) in anhydrous NMP (4 mL). The reaction mixture was slowly warmed to ambient temperature. After 16 h, the reaction mixture was diluted with diethyl ether and EtOAc (10:1) and washed successively with aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by RP-HPLC (2″ Dynamax C18, 40-100% ACN/water containing 0.1% HOAc over 30 min; Flow: 40 mL/min) to afford 270 mg (71%) of 64. Mass spectrum, m/z [509.2] (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08399683B2
Source dataset	uspto-grants-2013_03
ORD ID	ord-38a7582a04de4c62b8131c17bdb229d9
Source note	uspto-grants-2013_03