Tetrahydrofuran → (4R,5S)-4-Methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one

HRID 458030Notes

Reaction equation

HRID 458030 reaction equation
[CH3:1][C@H:2]([CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][C:5]([OH:7])=O.C(N(CC)CC)C.[CH3:18][C:19]([CH3:24])(C)[C:20](Cl)=[O:21].[Li+].[Cl-].[O:27]1[CH2:31][CH2:30][NH:29][C:28]1=O.[CH2:33]1[CH2:37]OC[CH2:34]1>>[CH3:31][C@@H:30]1[C@H:20]([C:19]2[CH:24]=[CH:37][CH:33]=[CH:34][CH:18]=2)[O:21][C:28](=[O:27])[N:29]1[C:5](=[O:7])[CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 6

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 433294Lithium ChlorideHCID 138003704-Methylheptanoic acid, (-)-

Product 1

HCID 57160957(4R,5S)-4-Methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one

Procedure

To the acid 99 (19 g, 0.132 mol) and triethylamine (49.9 g, 0.494 mol) in THF (500 mL) at 0° C. was added trimethylacetylchloride (20 g, 0.17 mol). After 1 hour LiCl (7.1 g, 0.17 mol) was added followed by the oxazolidinone (30 g, 0.17 mol). The mixture was warmed to room temperature and after 16 hours the filtrate was removed by filtration and the solution concentrated under reduced pressure. Flash chromatography (7:1 hexane/EtOAc) gave the product 100 as an oil. 31.5 g; 79%. [α]D=5.5 (c 1 in CHCl3). MS, m/z (relative intensity): 304 [M+H, 100%].

Workup

  1. customwas removed by filtration
  2. concentrationthe solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c7347a96ef448f79ecd912e99bfbc70
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

Loading…