Phenylacetylene → (4S,5S)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetylene	HCID 10821	—
Reactant	(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one	HCID 69083418	—
Reactant	(-)-(4S,5S)-4-(3-bromophenyl)-5-(3-methoxyphenyl)oxazolidin-2-one	HCID 69083858	—
Product	(4S,5S)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one	HCID 69081662	—

Reaction Steps

Prepared according to the same procedure as (+)-(4R,5R)-5-(3-methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one, starting with (−)-(4S,5S)-4-(3-bromophenyl)-5-(3-methoxyphenyl)oxazolidin-2-one and phenylacetylene. 1H-NMR (CDCl3, 500 MHz) δ 7.56 (m, 4H), 7.36-7.45 (m, 4H), 7.34 (m, 1H), 7.30 (m, 1H), 6.92-6.98 (m, 1H), 6.85-6.90 (m, 2H), 5.93 (bs, 1H), 5.31 (d, J=7.3, 1H), 4.78 (d, J=7.3, 1H), 3.84 (s, 3H). 13C-NMR (CDCl3, 126 MHz) δ 160.2, 158.6, 138.92, 138.85, 132.3, 131.8, 130.2, 129.6, 129.4, 128.7, 128.5, 126.4, 124.6, 122.9, 118.1, 115.0, 111.2, 90.6, 88.6, 85.9, 64.6, 55.5. Mass spec.: 370.14 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691821B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-18bb36e4b3d44ae0a14f3a50dccaa0b9
Source note	uspto-grants-2014_04