Triethylamine → 3-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

HRID 1387424ノート

反応式

HRID 1387424 の反応式
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[O:6][CH2:5][CH2:4][O:3]1.CCN(CC)CC.C(Cl)(=O)C(C)(C)C.[O:28]1[CH2:32][CH2:31][NH:30][C:29]1=[O:33].[Li]CCCC.[Li]>C(OCC)(=O)C.C1COCC1>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([N:30]2[CH2:31][CH2:32][O:28][C:29]2=[O:33])=[O:13])[O:3][CH2:4][CH2:5][O:6]1

参加物

9

反応物 6

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-OxazolidinoneHCID 3028194LithiumHCID 154537565-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoic acidHCID 178418339Butyllithium

生成物 1

HCID 154537573-[5-(2-Methyl-[1,3]dioxolan-2-yl)-pentanoyl]-oxazolidin-2-one

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 2-2 (16.0 g, 85.5 mmol), NEt3 (13.1 ml, 94.1 mmol) and THF (400 mL) at −78° C. was added pivaloyl chloride (11.6 ml, 94.1 mmol). The mixture was warmed to 0° C. for 1.0 h and then recooled to −78° C. To a stirred solution of 2-oxazolidinone (9.3 g, 106.9 mmol) and THF (200 ml) at −78° C. was added nBuLi (43.0 ml, 106.9 mmol, 2.5M in hexanes) dropwise over 10 minutes. After 20 minutes, the lithium reagent was transferred to the mixed anhydride via cannula. After 10 minutes, the reaction was warmed to 0° C. for 1.0 h. The mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes) to give 2-3 as a colorless foam.

後処理

  1. customrecooled to −78° C
  2. waitAfter 10 minutes
  3. temperaturethe reaction was warmed to 0° C. for 1.0 h
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customremoval of the solvent
  7. customthe residue was chromatographed (silica gel, 40%-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-42d471083ffa432c8c5f454900e0bf85
出典データセット
uspto-grants-2001_07
特許番号
US06268378B1

反応ノート

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