ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Di-tert-butyl dicarbonate → 17beta-Carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one

HRID 1077588
ノート
印刷プレビュー

反応式

HRID 1077588 の反応式
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([O:24][Si](C(C)C)(C(C)C)C(C)C)[CH2:17][CH2:18]1)=[N:13][CH2:12]3)([O:3][CH3:4])=[O:2].C([O:39][C:40](OC(OC(C)(C)C)=O)=[O:41])(C)(C)C.[F-].C([N+](C[CH2:65][CH2:66][CH3:67])(CCCC)CCCC)CCC.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=C[CH:78]=1.[NH+]1C=CC=CC=1>N1C=CC=CC=1.O1CCCC1.O>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH2:7][C:40]([OH:41])=[O:39])[C@:19]1([CH3:20])[C:18](=[CH:17][C:16](=[O:24])[CH2:15][CH2:14]1)[N:13]([C:66]([CH3:65])([CH3:67])[CH3:78])[CH2:12]3)([O:3][CH3:4])=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 90495Di-tert-butyl dicarbonateHCID 2724130Cornforth reagentHCID 2724141Tetrabutylammonium FluorideHCID 1045826517beta-Carbomethoxy-3beta-triisopropylsilyloxy-6-azaandrost-5-ene

生成物 1

HCID 8674903517beta-Carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 1049Pyridine溶媒2 回
HCID 8028Tetrahydrofuran溶媒

実験手順

Crude 17β-carbomethoxy-3β-triisopropylsilyloxy-6-azaandrost-5-ene (66 g, 0.135 mol)is dissolved in pyridine (500 mL), treated with di-t-butyldicarbonate (150 g, 0.69 mol) and allowed to stir overnight. The pyridine is removed by rotary evaporation and tetrabutylammonium fluoride (500 mL, 1M, 0.5 mol) in tetrahydrofuran (THF) added carefully and the reaction heated to reflux for 5 min. The THF is removed by rotary evaporation, the residue dissolved in ethyl acetate (500 mL), washed cautiously with water, saturated aqueous NaCl, dried with MgSO4 and concentrated. This material is dissolved in DMF (500 mL), is treated with pyridinium dichromate (153 g, 0.41 mol) and allowed to stir overnight. The reaction is poured into water (700 mL) and extracted with ethyl acetate (2×500 mL). The combined extracts are washed with water, 5% aqueous CuSO4, saturated aqueous NaCl, dried over MgSO4, concentrated and flash chromatographed (0-60%, diethyl ether/hexanes) to give 17β-carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one as an off-white foam; yield: 37.5 g (64%); FAB mass spec. MH+ 432.

後処理

  1. additionadded carefully
  2. temperaturethe reaction heated
  3. temperatureto reflux for 5 min
  4. customThe THF is removed by rotary evaporation
  5. dissolutionthe residue dissolved in ethyl acetate (500 mL)
  6. washwashed cautiously with water, saturated aqueous NaCl
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated
  9. dissolutionThis material is dissolved in DMF (500 mL)
  10. stirringto stir overnight
  11. extractionextracted with ethyl acetate (2×500 mL)
  12. washThe combined extracts are washed with water, 5% aqueous CuSO4, saturated aqueous NaCl
  13. dry with materialdried over MgSO4
  14. concentrationconcentrated
  15. customflash chromatographed (0-60%, diethyl ether/hexanes)

出典と根拠

ORDレコード
ord-e5de452256254dc2afa3e59d8969ae4a
出典データセット
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05543406

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート