Trifluoroacetic acid → (2R)-2-amino-2-methyl-N-[6-(3-methylchroman-5-yl)oxy-3-pyridyl]butanamide

HRID 527610ノート

反応式

HRID 527610 の反応式
[CH3:1][C@:2]([NH:26]C(=O)OC(C)(C)C)([C:5](=[O:25])[NH:6][C:7]1[CH:8]=[N:9][C:10]([O:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH:17]([CH3:24])[CH2:18][O:19]3)=[CH:11][CH:12]=1)[CH2:3][CH3:4].C(O)(C(F)(F)F)=O>ClCCl>[NH2:26][C@:2]([CH3:1])([CH2:3][CH3:4])[C:5]([NH:6][C:7]1[CH:8]=[N:9][C:10]([O:13][C:14]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:15]=2[CH2:16][CH:17]([CH3:24])[CH2:18][O:19]3)=[CH:11][CH:12]=1)=[O:25]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86698444tert-butyl N-[(1R)-1-methyl-1-[[6-(3-methylchroman-5-yl)oxy-3-pyridyl]carbamoyl]propyl]carbamate2 回

生成物 1

HCID 67959932(2R)-2-amino-2-methyl-N-[6-(3-methylchroman-5-yl)oxy-3-pyridyl]butanamide収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

In a 50 mL round-bottomed flask tert-butyl N-[(1R)-1-methyl-1-[[6-(3-methylchroman-5-yl)oxy-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 146, 55.8 mg, 0.104 mmol) was dissolved in Dichloromethane (3 mL) to give a pale yellow solution. The reaction mixture was cooled at 0° C. and TFA (2 mL, 26.0 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was evaporated in vacuo to give the crude product as a yellow oil. The sample was charged on a 2 g SCX cartridge. It was then flushed with 36 mL of MeOH followed by 25 mL of 2M solution of ammonia in MeOH. The ammonia eluate was evaporated in vacuo affording the title compound (32.9 mg) as pale yellow oil.

後処理

  1. customto give a pale yellow solution
  2. customThe reaction mixture was evaporated in vacuo
  3. customto give the crude product as a yellow oil
  4. additionThe sample was charged on a 2 g SCX cartridge
  5. customIt was then flushed with 36 mL of MeOH
  6. customThe ammonia eluate was evaporated in vacuo

出典と根拠

ORDレコード
ord-e086e393c35848d297f62755dec84382
出典データセット
uspto-grants-2016_05
特許番号
US09346790B2

反応ノート

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