Sodium Carbonate → (S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidine-5-carboxylic acid

HRID 1511780

反応式

HRID 1511780 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@@H:14]([CH2:16][OH:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.C(OC[C@H]1OC1)(=[O:23])CCC.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=O)C.CC1(C)N([O])C(C)(C)CCC1.C([O-])([O-])=O.[Na+].[Na+]>CC(=O)OCC.O.CC#N>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([N:11]3[CH2:15][C@@H:14]([C:16]([OH:23])=[O:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 2724126TempoHCID 6999819(S)-(+)-Glycidyl butyrateHCID 21865429Bis(acetoxy)iodobenzeneHCID 66736976(S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-one

生成物 1

HCID 66736285(S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-2-oxo-oxazolidine-5-carboxylic acid収率 81%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 18373917Acetonitrile--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

To a solution of (S)-3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-5-hydroxymethyl-oxazolidin-2-one (enantiomeric antipode of intermediate 1.iii), prepared from (S)-glycidyl butyrate, 985 mg, 3.92 mmol) in 1:1 water/MeCN (20 mL) cooled to 0° C. was added diacetoxyiodobenzene (2.83 g, 2.2 eq) and TEMPO (122 mg, 0.2 eq). The mixture was stirred at 0° C. for 30 min and at rt overnight. EA and sat. Na2CO3 were added and the phases separated. The aq. layer was washed once more with EA and then carefully acidified with 1M aq. HCl. The aq. phase was then extracted 2× with EA. The combined org. layers were washed with brine and dried over MgSO4 and concentrated to afford the desired intermediate as colourless solid (847 mg, 81%).

後処理

  1. customthe phases separated
  2. washThe aq. layer was washed once more with EA
  3. extractionThe aq. phase was then extracted 2× with EA
  4. washlayers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-a9a04af59b57411bbe838ee8d77f2a07
出典データセット
uspto-grants-2012_07
特許番号
US08217029B2

関連ノート

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