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

HRID 1511780

반응식

HRID 1511780 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 18373917Acetonitrile--water (1/1)용매

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온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a9a04af59b57411bbe838ee8d77f2a07
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217029B2

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