HCID 54587249, 화합물 → Nimbidic acid

HRID 1087801노트

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HRID 1087801 반응식
C/C=C(\C([O:7][C@@H:8]1[C@:16]2([CH3:38])[C@@H:17]([CH2:33][C:34]([O:36]C)=[O:35])[C@:18]3([CH3:32])[C:22]4=[C:23]([CH3:31])[C@H:24]([C:26]5[CH:27]=[CH:28][O:29][CH:30]=5)[CH2:25][C@H:21]4[O:20][C@@H:19]3[C@H:14]3[C@H:15]2[C@:11]([CH3:39])([CH2:12][O:13]3)[C@H:10]([O:40]C(C)=O)[CH2:9]1)=O)/C>[OH-].[Na+].CO>[CH3:31][C:23]1[C@H:24]([C:26]2[CH:27]=[CH:28][O:29][CH:30]=2)[CH2:25][C@H:21]2[O:20][C@@H:19]3[C@@H:14]4[O:13][CH2:12][C@@:11]5([CH3:39])[C@H:15]4[C@:16]([CH3:38])([C@@H:8]([OH:7])[CH2:9][C@H:10]5[OH:40])[C@@H:17]([CH2:33][C:34]([OH:36])=[O:35])[C@:18]3([CH3:32])[C:22]=12

참가 물질

4

반응물 1

HCID 54587249HCID 54587249, 화합물

생성물 1

HCID 185704Nimbidic acid수율 69.8%

시약·촉매·용매 2

HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

실험 절차

Salannic acid (1c) was prepared by a modification of the method of de Silva et al. (1969), supra. Salannin (30 mg, 0.050 mmol) was dissolved in 2.0 mL of 0.5 N NaOH in 50% aqueous methanol and incubated at 60° C. for 6 h. The reaction mixture was poured onto 10 mL of 0.5 N HC1 and extracted three times with 10-mL portions of diethyl ether. The organic layers were combined, washed once with 10 mL of saturated aqueous sodium chloride, and rotary evaporated in vacuo. Purification of the crude product by silica gel preparative HPLC (solvent = isopropanol-n-hexane acetic acid, 10:90:1) yielded salannic acid (16 mg). The IR spectrum of salannic acid showed the loss of the absorptions at 1710, 1655, and 735 cm-1, assigned to the tigloyl group (Henderson et al., 1968; Butterworth, J. H., et al. J. Chem. Soc.. Perkin Trans. I. 1972, 1445-2450; Yamasaki and Klocke, unpublished data), and the appearance of a very broad, intense absorption at 3400 cm-1 characteristic of a carboxylic acid (Silverstein et al., Spectrometric Identification of Organic Compounds, 4th ed. Wiley, New York, 1981, pp. 204-208). All of the 1H-NMR absorptions of the tigloyl (δ1.81, 1.94, and 6.96), acetyl (δ1.94, and carbomethoxyl (δ3.24) groups had vanished.

후처리

  1. customSalannic acid (1c) was prepared by a modification of the method of de Silva et al. (1969), supra
  2. additionThe reaction mixture was poured onto 10 mL of 0.5 N HC1
  3. extractionextracted three times with 10-mL portions of diethyl ether
  4. washwashed once with 10 mL of saturated aqueous sodium chloride
  5. customrotary evaporated in vacuo
  6. customPurification of the crude product by silica gel preparative HPLC (solvent = isopropanol-n-hexane acetic acid, 10:90:1)

출처 및 근거

ORD 기록
ord-18a4a127f47341138a79f7bc38cdb8c1
출처 데이터셋
uspto-grants-1990_10
특허 번호
US04960791

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