4-Methyltestosterone → (3E,8R,9S,10R,13S,14S,17S)-3-(2-aminoethoxyimino)-4,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol;hydrochloride

HRID 1182858

反応式

HRID 1182858 の反応式
[CH3:1][C:2]1[C:18](=O)[CH2:17][CH2:16][C@@:15]2([CH3:20])[C:3]=1[CH2:4][CH2:5][C@@H:6]1[C@@H:14]2[CH2:13][CH2:12][C@@:11]2([CH3:21])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].[ClH:23].Cl.[NH2:25][CH2:26][CH2:27][O:28][NH2:29]>O1CCOCC1.O.[Cl-].[Na+].O>[ClH:23].[NH2:25][CH2:26][CH2:27][O:28]/[N:29]=[C:18]1/[C:2]([CH3:1])=[C:3]2[C@:15]([CH3:20])([CH2:16][CH2:17]/1)[C@@H:14]1[C@H:6]([C@H:7]3[C@@:11]([CH2:12][CH2:13]1)([CH3:21])[C@@H:10]([OH:22])[CH2:9][CH2:8]3)[CH2:5][CH2:4]2

参加物

6

反応物 2

HCID 2365364-MethyltestosteroneHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

生成物 1

HCID 87572473(3E,8R,9S,10R,13S,14S,17S)-3-(2-aminoethoxyimino)-4,10,13-trimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol;hydrochloride収率 74%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To a stirred solution of 4-methyltestosterone (203 mg) in dioxane (3.7 ml), a solution of 2-aminoethoxyamine dihydrochloride (259 mg) in water (2 ml) was rapidly added dropwise. After 24 h dioxane (20 ml) and brine (10 ml) were added and the mixture was stirred for 10 min. The phases were separated and the aqueous phase was extracted with dioxane (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated to dryness. The residue was triturated with Et2O for 5 h and the precipitate was filtered. The crude product was dissolved in water and freeze-dried to give the title compound (I-aa) as a white solid (197 mg, 74%).

後処理

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with dioxane (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was triturated with Et2O for 5 h
  8. filtrationthe precipitate was filtered
  9. dissolutionThe crude product was dissolved in water
  10. customfreeze-dried

出典と根拠

ORDレコード
ord-13deb6a225ea4150affda653fd66711f
出典データセット
uspto-grants-2014_03
特許番号
US08664210B2

関連ノート

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