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

HRID 1640519

반응식

HRID 1640519 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(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:21])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:21])=[O:17])[O:13][C:12]3=[O:18])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 2724126TempoHCID 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 81.5%

시약·촉매·용매 2

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

반응 조건

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 (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 were separated. The aq. layer was washed once more with EA and then carefully acidified with 1M HCl. The water phase was then extracted twice with EA. The combined org. layers were washed with brine and dried over MgSO4 and concentrated to afford the title intermediate as a colourless solid (847 mg, 81% yield).

후처리

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

출처 및 근거

ORD 기록
ord-77ba1dbf9cad4bb3902789dce93097a6
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08114867B2

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