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Methanol → 9-(((2R)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-ol

HRID 1972472
ノート
印刷プレビュー

反応式

HRID 1972472 の反応式
[N+](C1SC(S([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[N:23]=[CH:22][C:21]([C:24]([OH:33])([C:29]([F:32])([F:31])[F:30])[C:25]([F:28])([F:27])[F:26])=[CH:20][N:19]=3)[C@@H:14]([CH2:34][N:35]3[CH:40]4[CH2:41][CH:42]([OH:44])[CH2:43][CH:36]3[CH2:37][O:38][CH2:39]4)[CH2:13]2)(=O)=O)=CC=1)([O-])=O.[N+](C1SC(S([N:56]2[CH2:61][CH2:60][N:59]([C:62]3[N:67]=[CH:66][C:65]([C:68]([OH:77])([C:73]([F:76])([F:75])[F:74])[C:69]([F:72])([F:71])[F:70])=[CH:64][N:63]=3)[C@@H:58]([CH2:78][N:79]3[CH:84]4[CH2:85][C:86](=[O:88])[CH2:87][CH:80]3[CH2:81][O:82][CH2:83]4)[CH2:57]2)(=O)=O)=CC=1)([O-])=O.[OH-].[K+].CO>O>[F:32][C:29]([F:30])([F:31])[C:24]([C:21]1[CH:20]=[N:19][C:18]([N:15]2[CH2:16][CH2:17][NH:12][CH2:13][C@@H:14]2[CH2:34][N:35]2[CH:36]3[CH2:43][CH:42]([OH:44])[CH2:41][CH:40]2[CH2:39][O:38][CH2:37]3)=[N:23][CH:22]=1)([OH:33])[C:25]([F:26])([F:27])[F:28].[F:76][C:73]([F:74])([F:75])[C:68]([C:65]1[CH:64]=[N:63][C:62]([N:59]2[CH2:60][CH2:61][NH:56][CH2:57][C@@H:58]2[CH2:78][N:79]2[CH:80]3[CH2:87][C:86](=[O:88])[CH2:85][CH:84]2[CH2:83][O:82][CH2:81]3)=[N:67][CH:66]=1)([OH:77])[C:69]([F:70])([F:72])[F:71]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 866703529-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-olHCID 866703539-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one

生成物 2

HCID 86670354
9-(((2R)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-ol
HCID 866703559-(((2R)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 25-mL round-bottomed flask was charged with a 1:1 mixture of 9-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-ol (endo) and 9-(((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (300 mg, 0.44 mmol, Example 98, Step 5), potassium hydroxide (749 mg, 13.34 mmol), MeOH (5 mL) and water (2 mL) and was stirred at room temperature for 30 min. The solvent was removed in vacuo and then diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The organic layers were dried (Na2SO4), filtered, and concentrated to give 9-(((2R)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-ol (endo) and 9-(((2R)-1-(5-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-2-pyrimidinyl)-2-piperazinyl)methyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one (215 mg) which were used without purification.

後処理

  1. customThe solvent was removed in vacuo
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bce106984a54402a80ef58ea7bb58892
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08431563B2

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