Hydrochloric Acid → 1-[(E)-[(E)-3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]prop-2-enylidene]amino]guanidine

HRID 1080628ノート

反応式

HRID 1080628 の反応式
C(=O)(O)O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].Cl.[OH:11][C@H:12]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:14]([CH2:15][CH2:16][C@@H:17]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@:18]3([OH:35])[CH2:19][CH2:20][C@@H:21]2/[CH:22]=[CH:23]/[CH:24]=O)[CH2:13]1>O.O1CCOCC1>[NH:6](/[N:5]=[CH:24]/[CH:23]=[CH:22]/[C@H:21]1[CH2:20][CH2:19][C@:18]2([OH:35])[C@H:17]3[C@H:29]([CH2:28][CH2:27][C@:26]12[CH3:34])[C@:30]1([CH3:33])[C@@H:14]([CH2:13][C@@H:12]([OH:11])[CH2:32][CH2:31]1)[CH2:15][CH2:16]3)[C:7]([NH2:9])=[NH:8]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10736377(E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxaldehydeHCID 178513185HCID 178513185、化合物

生成物 1

HCID 1765255681-[(E)-[(E)-3-[(3S,5R,8R,9S,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]prop-2-enylidene]amino]guanidine収率 65.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回

実験手順

A mixture of 1.05 g of aminoguanidine hydrogencarbonate in 23 ml of water and 70 ml of dioxane was made acid to pH 3 with 3N HCl. A solution of 2.08 g of (E)-3β,14β-dihydroxy-5β-pregn-20-ene-21-carboxaldehyde (Fullerton D. S. et al., J. Med. Chem., 1976, 19, 1330) in 20 ml of dioxane was added at room temperature. After 3 days the mixture was evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 80/20/3 as the eluant; the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with diethyl ether and ethanol to give 1.58 g of the title compound (I-aa) as a white solid.

後処理

  1. customAfter 3 days the mixture was evaporated to dryness under reduced pressure
  2. customThe crude product was purified by flash chromatography (SiO2)
  3. additionthe fractions containing the title compound
  4. customwere collected
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-ac32a25b35154743b99dbaefbf723756
出典データセット
uspto-grants-1996_12
特許番号
US05583127

反応ノート

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