Ethyl Acetate → HCID 69584937, compound

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Pyrazine	HCID 9261	—
Reactant	tert-Butyl pyrimidin-2-ylcarbamate	HCID 10976384	—
Reactant	3-(4-(1-(2(S),3-Dihydroxypropanoyl)-1,2,5,6-tetrahydropyrid-4-yl)-3,5-difluorophenyl)-5(S)-pyrazin-2-ylaminomethyloxazolidin-2-one	HCID 20725661	—
Solvent	Dichloromethane	HCID 6344	—
Product	HCID 69584937	HCID 69584937	—

Reaction Steps

Essentially the technique for the appropriate intermediate of Example 22 was used, but substituting 2-(t-butoxycarbonylamino)pyrimidine (293 mg, 1.5 mM) for the pyrazine analogue. To complete the reaction, heating at 80° for 1 hour was necessary, and the chromatography was carried out with a gradient from 0% to 50% ethyl acetate in dichloromethane containing 2% triethylamine. Relevant fractions were combined to give the desired product (427 mg). NMR (DMSO-d6) δ: 1.32 (s, 3H); 1.34 (s, 3H); 1.41 (s, 9H); 2.30 (br, 1H); 2.38 (br, 1H); 3.67 (t, 1H); 3.75 (m, 1H); 3.87 (dd, 1H); 4.00-4.33 (overlapping m, 7H); 4.90 (dd, 1H); 5.01 (m, 1H); 5.87 (s, 1H); 7.27 (t, 1H); 7.31 (d, 2H); 8.73 (d, 2H). MS (ESP): 616 (MH+) for C30H35F2N5O7

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06734200B1
Source dataset	uspto-grants-2004_05
ORD ID	ord-cae631f3640444859527e0797a7fa7b4
Source note	uspto-grants-2004_05