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Ammonia → (S)-4-Amino-N-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216924
ノート
印刷プレビュー

反応式

HRID 216924 の反応式
[C:1]([C@@H:3]([NH:19][C:20]([C:22]1([NH:28]C(=O)OC(C)(C)C)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=2)=[CH:7][CH:6]=1)#[N:2].O.N>C(O)=O>[NH2:28][C:22]1([C:20]([NH:19][C@H:3]([C:1]#[N:2])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[CH:12]=3)=[CH:9][CH:10]=2)=[O:21])[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 222AmmoniaHCID 962WaterHCID 59568588(S)-tert-butyl 4-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 49783746(S)-4-Amino-N-(1-cyano-2-(3'-cyanobiphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide収率 40%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
36 °C

実験手順

(S)-tert-butyl 4-(1-cyano-2-(3′-cyanobiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 8, step (ii), 282 mg) in formic acid (1.5 mL) was stirred at room temperature for 5 h, warmed at 36° C. for 30 mins then stirred at room temperature overnight. Water was added and the cooled solution was made basic with 0.880 ammonia and then extracted (×3) with dichloromethane. The combined organic extracts were dried over magnesium sulphate, filtered and the solvent was evaporated to yield an oil which was purified by chromatography on silica using 80% ethyl acetate in isohexane as eluent and then crystallised from isopropanol to yield a solid. The solid was washed with diethyl ether and dried to afford the titled compound (89 mg).

後処理

  1. extractionextracted (×3) with dichloromethane
  2. dry with materialThe combined organic extracts were dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customto yield an oil which
  6. customwas purified by chromatography on silica using 80% ethyl acetate in isohexane as eluent
  7. customcrystallised from isopropanol
  8. customto yield a solid
  9. washThe solid was washed with diethyl ether
  10. customdried

出典と根拠

ORDレコード
ord-9641d5bc9e7345cbb8b7009d1582c899
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193239B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート