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Trifluoroacetic acid → (2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide

HRID 527666
ノート
印刷プレビュー

反応式

HRID 527666 の反応式
[CH3:1][C:2]1([CH3:32])[CH2:6][C:5]2[C:7]([O:11][C:12]3[N:17]=[CH:16][C:15]([NH:18][C:19]([C@H:21]([NH:24]C(=O)OC(C)(C)C)[CH2:22][CH3:23])=[O:20])=[CH:14][CH:13]=3)=[CH:8][CH:9]=[CH:10][C:4]=2[O:3]1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:24][C@H:21]([CH2:22][CH3:23])[C:19]([NH:18][C:15]1[CH:16]=[N:17][C:12]([O:11][C:7]2[C:5]3[CH2:6][C:2]([CH3:1])([CH3:32])[O:3][C:4]=3[CH:10]=[CH:9][CH:8]=2)=[CH:13][CH:14]=1)=[O:20]
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 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86698460tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate2 回

生成物 1

HCID 67958761(2R)-2-amino-N-{6-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-3-pyridinyl}butanamide収率 91.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a solution of tert-butyl N-[(1R)-1-[[6-[(2,2-dimethyl-3H-benzofuran-4-yl)oxy]-3-pyridyl]carbamoyl]propyl]carbamate (Intermediate 208, 14 mg, 0.032 mmol) in dry dichloromethane (1 ml) at 0° C., TFA (98 μl, 1.268 mmol) was slowly added and the reaction mixture was stirred for 4 hours at the same temperature. Some more dichloromethane (4 ml) was added to the reaction mixture. An aqueous saturated aqueous solution of NaHCO3 was then added while the pH was allowed to reach ˜8. Two phases were separated and the aqueous one was further extracted with DCM (3×3 ml). Combined organic layers were dried over Na2SO4, filtrated and evaporated affording the title compound (10 mg).

後処理

  1. customTwo phases were separated
  2. extractionthe aqueous one was further extracted with DCM (3×3 ml)
  3. dry with materialCombined organic layers were dried over Na2SO4
  4. filtrationfiltrated
  5. customevaporated

出典と根拠

ORDレコード
ord-179f9c0fc39b40dbbc86416d69c536ed
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346790B2

反応ノート

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