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

HRID 2362437Notes

Reaction equation

HRID 2362437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@H:9]2[O:13][C:12](=[O:14])[NH:11][C@@H:10]2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:6]=[CH:7][CH:8]=1.BrC1C=C([C@H]2[C@H](C3C=CC=C(OC)C=3)OC(=O)N2)C=CC=1.C1(C#C)C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C@@H:9]2[O:13][C:12](=[O:14])[NH:11][C@H:10]2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[C:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 10821PhenylacetyleneHCID 69083418(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-oneHCID 69083858(-)-(4S,5S)-4-(3-bromophenyl)-5-(3-methoxyphenyl)oxazolidin-2-one

Product 1

HCID 69081662(4S,5S)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one

Procedure

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)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-18bb36e4b3d44ae0a14f3a50dccaa0b9
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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