(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate → (S)-4-Amino-N-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide

HRID 216907ノート

反応式

HRID 216907 の反応式
[C:1]([C@@H:3]([NH:22][C:23]([C:25]1([NH:31]C(=O)OC(C)(C)C)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:24])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>C(O)=O>[NH2:31][C:25]1([C:23]([NH:22][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][C:14]([S:17]([CH2:20][CH3:21])(=[O:19])=[O:18])=[CH:13][CH:12]=3)=[CH:9][CH:10]=2)=[O:24])[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

参加物

3

反応物 1

HCID 59568561(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 49783665(S)-4-Amino-N-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide収率 52.9%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
50 °C

実験手順

To (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (v(ii)), 920 mg) was added formic acid (3 mL) and the mixture heated to 50° C. for 30 min. The mixture was evaporated to dryness, dissolved in methanol (9 mL) and purified on reverse phase HPLC eluting with 25 to 95% methanol in 0.1% TFA on a Waters SunFire column. The material was converted to free base by evaporating the relevant fractions, dissolving in dichloromethane (20 mL) and shaking with saturated sodium bicarbonate solution (20 mL). The dichloromethane was dried and evaporated to afford the titled compound as a solid (397 mg).

後処理

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in methanol (9 mL)
  3. custompurified on reverse phase HPLC
  4. washeluting with 25 to 95% methanol in 0.1% TFA on a Waters SunFire column
  5. customby evaporating the relevant fractions
  6. dissolutiondissolving in dichloromethane (20 mL)
  7. dry with materialThe dichloromethane was dried
  8. customevaporated

出典と根拠

ORDレコード
ord-ec13180bea404d1b84a075428da64433
出典データセット
uspto-grants-2012_06
特許番号
US08193239B2

反応ノート

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