Oxalic Acid → HCID 131724378, 화합물

HRID 49410노트

반응식

HRID 49410 반응식
CO[C:3]1[CH2:4][C:5]2[CH2:6][C@@H:7]([CH3:24])[C@@H:8]3[C@@H:17]([C:18]=2[CH2:19][CH:20]=1)[CH2:16][CH2:15][C@@:13]1([CH3:14])[C@:9]23[CH2:23][C@@H:10]2[CH2:11][C@H:12]1[CH2:21]O.C(O)(=O)[C:26](O)=[O:27].C(=O)([O-])[OH:32].[Na+]>CO.O1CCCC1.O>[OH:27][CH2:26][CH2:21][C@@H:12]1[CH2:11][C@H:10]2[CH2:23][C@@:9]32[C@H:8]2[C@H:17]([CH2:16][CH2:15][C@:13]13[CH3:14])[C:18]1[CH2:19][CH2:20][C:3](=[O:32])[CH2:4][C:5]=1[CH2:6][C@H:7]2[CH3:24]

참가 물질

7

반응물 3

HCID 971Oxalic AcidHCID 516892Sodium BicarbonateHCID 69625019(7alpha,14beta,15beta,17alpha)-3-Methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol

생성물 1

HCID 131724378HCID 131724378, 화합물

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (7α,14β,15β,17α)-3-methoxy-7-methyl-14,15-methyleneestra-2,5(10)-diene-17-methanol (Example 1, step vi; 7.38 g) in a mixture of methanol (68 ml) and tetrahydrofuran (48 ml) was treated with a solution of oxalic acid (2.38 g) in water (40 ml). After 1 h stirring at room temperature, the reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate and the product was extracted into ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (7α,14β,15β,17α)-17-(hydroxyethyl)-7-methyl-14,15-methyleneestr-5(10)-en-3-one (4.27 g). 1H NMR (CDCl3) δ3.69 (m, 1H), 3.51 (t, 1H, J=9.0 Hz), 2.72 (bs, 2H), 2.46 (bs, 2H), 1.04 (s, 3H), 0.69 (d, 3H, J=7.1 Hz), 0.48(dd, 1H, J=8.3 and 5.1 Hz), 0.27 (dd, 1H, J=5.1 and 3.1 Hz).

후처리

  1. extractionthe product was extracted into ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d3ce938e8ba948cdb819560530d83ab7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706700B2

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