HCID 54587249、化合物 → Nimbidic acid

HRID 1087801ノート

反応式

HRID 1087801 の反応式
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

参加物

4

反応物 1

HCID 54587249HCID 54587249、化合物

生成物 1

HCID 185704Nimbidic acid収率 69.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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 I. 1972, 1445-2450; Yamasaki and Klocke, unpublished data), and the appearance of a very broad, intense absorption at 3400 cm-1 characteristic of a carboxylic acid (Silverstein et al., Spectrometric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.

後処理

  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)

出典と根拠

ORDレコード
ord-18a4a127f47341138a79f7bc38cdb8c1
出典データセット
uspto-grants-1990_10
特許番号
US04960791

反応ノート

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