(S)-4-methylnonanoic acid → (4R,5S)-4-Methyl-3-((S)-4-methyl-nonanoyl)-5-phenyl-oxazolidin-2-one

HRID 722883Notes

Reaction equation

HRID 722883 reaction equation
[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:24])[CH2:15][CH2:16][C@H:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C[C@@H](CCCCC)CCC(O)=O>>[CH3:1][C@@H:2]1[C@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:24])[CH2:15][CH2:16][C@@H:17]([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 6997342(S)-4-methylnonanoic acidHCID 57037638(4R,5S)-4-Methyl-3-((R)-4-methyl-nonanoyl)-5-phenyl-oxazolidin-2-one

Product 1

HCID 57038538(4R,5S)-4-Methyl-3-((S)-4-methyl-nonanoyl)-5-phenyl-oxazolidin-2-oneYield 100%

Procedure

A procedure similar to that used to prepare compound 155 was used except that (S)-4-methylnonanoic acid 163 (5.56 g, 32.27 mmol) was used as a reactant to give 164 as an oil (10.70 g 100%). 1H NMR (400 MHz, CDCl3) δ 7.42–7.34 (m, 3H), 7.28 (d, J=6.59 Hz, 2H), 5.64 (d, J=7.33 Hz, 1H), 4.74 (quint, J=6.78 Hz, 1H), 2.94–2.85 (m, 2H), 1.73–1.67 (m, 1H), 1.47–1.43 (m, 1H), 1.39–1.22 (m, 7H), 0.90–0.84 (m, 8H).

Sources & evidence

ORD record
ord-5d6ef5c5e91a4b1ea9ebfa1e603f2474
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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