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Trifluoroacetic acid → 2-Amino-N-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-yl)-2-methylpropanamide

HRID 1036703
ノート
印刷プレビュー

反応式

HRID 1036703 の反応式
[CH2:1]([O:8][CH2:9][C@@H:10]([NH:30][C:31](=[O:43])[C:32]([NH:35]C(=O)OC(C)(C)C)([CH3:34])[CH3:33])[C:11]([N:13]1[CH2:17][CH2:16][C:15]2([CH:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:20][N:19]([CH3:28])[C:18]2=[O:29])[CH2:14]1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[NH2:35][C:32]([CH3:34])([CH3:33])[C:31]([NH:30][C@H:10]([CH2:9][O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:11]([N:13]1[CH2:17][CH2:16][C:15]2([CH:21]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][N:19]([CH3:28])[C:18]2=[O:29])[CH2:14]1)=[O:12])=[O:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 6422Trifluoroacetic acid2 回HCID 71060634tert-Butyl 1-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

生成物 1

HCID 710605682-Amino-N-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-yl)-2-methylpropanamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回
HCID 6344Dichloromethane溶媒

実験手順

A solution of tert-butyl 1-((2R)-3-(benzyloxy)-1-(7-methyl-6-oxo-9-phenyl-2,7-diazaspiro[4.4]nonan-2-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate (step 3) (206.5 mg) in DCM (4 mL) was treated with TFA (537 uL, 6.97 mmol). The reaction mixture was stirred at room temperature for 2 days. A further portion of TFA (2 ml) was added and stirring continued for 20 minutes. The mixture was concentrated in vacuo to afford a colourless oil. The oil was dissolved in MeOH and applied to a 10 g pre-wetted (MeOH) SCX-2 cartridge. The column was washed with MeOH (70 mL) and the product was eluted with 2M NH3 in MeOH (70 mL). The clean fractions were concentrated in vacuo to afford a colourless oil. The oil was further purified by mass-directed LC-MS to afford the title compound;

後処理

  1. stirringstirring
  2. waitcontinued for 20 minutes
  3. concentrationThe mixture was concentrated in vacuo
  4. customto afford a colourless oil
  5. washThe column was washed with MeOH (70 mL)
  6. washthe product was eluted with 2M NH3 in MeOH (70 mL)
  7. concentrationThe clean fractions were concentrated in vacuo
  8. customto afford a colourless oil
  9. customThe oil was further purified by mass-directed LC-MS

出典と根拠

ORDレコード
ord-701f6aca46004b9fa4836dcd91cb80fe
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546416B2

反応ノート

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