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

HRID 216949ノート

反応式

HRID 216949 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][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)#[N:2]>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:10]=[CH:9][C:8]([C:11]3[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=3)=[CH:7][CH:6]=2)=[O:21])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

参加物

3

反応物 1

HCID 59568628(S)-tert-Butyl 4-(1-cyano-2-(4'-methoxybiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 49783829(S)-4-Amino-N-(1-cyano-2-(4'-methoxybiphenyl-4-yl)ethyl)tetrahydro-2H-pyran-4-carboxamide収率 95.8%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

(S)-tert-Butyl 4-(1-cyano-2-(4′-methoxybiphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 20, step (i), 120 mg) was dissolved in formic acid (3 mL) and the mixture stirred at room temperature for 3 h. The mixture was evaporated to dryness, dissolved in methanol (10 mL), re-evaporated to dryness, dissolved in methanol (5.5 mL) and purified on reversed phase HPLC eluting with methanol in 0.1% aqueous TFA on a Water's SunFire column. The material was converted to free base by evaporating the relevant fractions, dissolving in ethyl acetate (20 mL) and extracted with saturated sodium bicarbonate solution (20 mL). The sodium bicarbonate solution was further extracted with ethyl acetate (20 mL). The combined ethyl acetate extracts were dried and evaporated to afford the titled compound (91 mg).

後処理

  1. customThe mixture was evaporated to dryness
  2. dissolutiondissolved in methanol (10 mL)
  3. customre-evaporated to dryness
  4. dissolutiondissolved in methanol (5.5 mL)
  5. custompurified on reversed phase HPLC
  6. washeluting with methanol in 0.1% aqueous TFA on a Water's SunFire column
  7. customby evaporating the relevant fractions
  8. dissolutiondissolving in ethyl acetate (20 mL)
  9. extractionextracted with saturated sodium bicarbonate solution (20 mL)
  10. extractionThe sodium bicarbonate solution was further extracted with ethyl acetate (20 mL)
  11. dry with materialThe combined ethyl acetate extracts were dried
  12. customevaporated

出典と根拠

ORDレコード
ord-ebed50e99afc4458933d1b42fca0ba36
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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