Trifluoroacetic acid → methyl (1S)-2-methyl-1-({2-[4-(2-pyridinyl)benzyl]hydrazino}carbonyl)propylcarbamate

HRID 643067노트

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HRID 643067 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:22]=[CH:21][C:10]([CH2:11][NH:12][NH:13][C:14]([O:16]C(C)(C)C)=O)=[CH:9][CH:8]=1.FC(F)(F)[C:25]([OH:27])=[O:26].[CH:30](N(C(C)C)CC)(C)C.CCOP(O[N:48]1N=N[C:52]2C=CC=[CH:56][C:51]=2[C:49]1=O)(OCC)=O>ClCCl>[CH3:52][CH:51]([CH3:56])[C@H:49]([NH:48][C:25](=[O:26])[O:27][CH3:30])[C:14]([NH:13][NH:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:22][CH:21]=1)=[O:16]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 9796325tert-Butyl 2-(4-(pyridin-2-yl)benzyl)hydrazinecarboxylate

생성물 1

HCID 91615834methyl (1S)-2-methyl-1-({2-[4-(2-pyridinyl)benzyl]hydrazino}carbonyl)propylcarbamate수율 47%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

A solution of Example 4B (0.18 g, 0.6 mmol) in dichloromethane:trifluoroacetic acid (4 mL, 1:1) was stirred at 25° C. for 1 h, and the solvents were evaporated. This material was dissolved in THF (1 mL) and treated with diisopropylethyl amine (0.31 mL, 3 equivalents), DEPBT (0.36 g, 2 equivalents), and Example 18A (0.105 g, 1 equivalent), stirred at 25° C. for 3 h. The mixture was partitioned between dichloromethane and 10% sodium carbonate, the organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 2% methanol/chloroform to give 0.1 g (47%) of the title compound.

후처리

  1. customthe solvents were evaporated
  2. dissolutionThis material was dissolved in THF (1 mL)
  3. customThe mixture was partitioned between dichloromethane and 10% sodium carbonate
  4. customthe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvents were evaporated
  9. customThe crude residue was purified

출처 및 근거

ORD 기록
ord-78d62214a5224b799cfb2c7563973491
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696226B2

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