Triethylamine → [(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Tert-butoxycarbonylalanine	HCID 85082	—
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 67390310	HCID 67390310	—
Solvent	Dichloromethane	HCID 6344	—
Product	[(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester	HCID 67396076	80.1%

Reaction Steps

To a suspension of the (S)-2-tert-Butoxycarbonylamino-propionic acid (43 mg, 0.23 mmol), HATU (99 mg, 0.26 mmol), and 1-Pyrimidin-2-yl-cyclopropylamine dihydrochloride (45 mg, 0.22 mmol) in CH2Cl2 (1.5 mL) was added triethylamine (0.12 mL, 0.87 mmol). The reaction was stirred at room temperature for 22 h, diluted with CH2Cl2 (7 mL) and then washed with saturated aqueous NaHCO3 (2×6 mL) and brine (1×6 mL). The organic phase was dried with MgSO4 and concentrated to afford 54 mg of [(S)-1-(1-Pyrimidin-2-yl-cyclopropylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester as white solid, m/z 307.56 [M+1]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08552205B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-154389db62b24dbfab6f92281d580914
Source note	uspto-grants-2013_10