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

HRID 527610노트

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HRID 527610 반응식
[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]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86698444tert-butyl N-[(1R)-1-methyl-1-[[6-(3-methylchroman-5-yl)oxy-3-pyridyl]carbamoyl]propyl]carbamate2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e086e393c35848d297f62755dec84382
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346790B2

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