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Formaldehyde → Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

HRID 1289224
ノート
印刷プレビュー

反応式

HRID 1289224 の反応式
C=O.[F:3][C:4]1[CH:23]=[C:22]([NH:24][CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:10]=1[F:19])=[O:7].[C:48]([BH3-])#N.[Na+].O>C(O)(=O)C>[F:3][C:4]1[CH:23]=[C:22]([N:24]([CH3:48])[CH:25]2[C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][C:28]=3[CH2:27][CH2:26]2)[N:35]=[C:34]([CH3:38])[N:33]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:45])[CH3:44])[C:32]4=[O:47])[CH:21]=[CH:20][C:5]=1[C:6]([O:8][C:9]1[C:10]([F:19])=[C:11]([F:18])[C:12]([F:17])=[C:13]([F:16])[C:14]=1[F:15])=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 19066345Pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

生成物 1

HCID 19066320Pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

An aqueous solution of formaldehyde (37% weight/volume, 17.55 ml) was added dropwise during 15 minutes to a stirred solution of pentafluorophenyl o-fluoro-p-[N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (13 g), prepared as described in Example 1, in glacial acetic acid (100 ml). The mixture was stirred at ambient temperature for 1 hour. Sodium cyanoborohydride (1.36 g) was added portionwise during 30 minutes and the resultant mixture was stirred at ambient temperature for 2 hours. The mixture was poured onto a mixture of ice and water (500 ml) and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The product was purified by column chromatography using increasingly polar mixtures of hexane and ethyl acetate as eluant. There was thus obtained pentafluorophenyl o-fluoro-p-[N-methyl-N-((6RS)-2-methyl-4-oxo-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl)amino]benzoate (11 g);

後処理

  1. customprepared
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. customThe product was purified by column chromatography
  6. temperatureusing increasingly polar mixtures of hexane and ethyl acetate as eluant

出典と根拠

ORDレコード
ord-437402b1b15541b4b1c2f3756e2da3c2
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05747499

反応ノート

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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