Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → Methyl N-(Benzo[b][1,8]napthyridin-2(1H)-one 3-yl)-N-(2-boc-aminoethyl)glycinate

HRID 987893ノート

反応式

HRID 987893 の反応式
[C:1]([CH:8]([NH2:16])[CH2:9][NH:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:17]1[C:26]2[N:25]=[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]3=[CH:22][C:21]=2[CH:20]=[CH:19][C:18]1=[O:31].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH:17]1[C:26]2[N:25]=[C:24]3[CH:27]=[CH:28][CH:29]=[CH:30][C:23]3=[CH:22][C:21]=2[CH:20]=[C:19]([N:10]([CH2:9][CH:8]([NH2:16])[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:18]1=[O:31]

参加物

5

反応物 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 5355541Benzo[b][1,8]naphthyridin-2(1H)-oneHCID 53740519Methyl N-(2-Boc-aminoethyl)glycinate

生成物 1

HCID 86759167Methyl N-(Benzo[b][1,8]napthyridin-2(1H)-one 3-yl)-N-(2-boc-aminoethyl)glycinate収率 23.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl N-(2-Boc-aminoethyl)glycinate (0.812 g, 3.5 mmol) was dissolved in DMF (10 mL) and benzo[b][1,8]napthyridin-2(1H)-one 3 acetic acid (883 mg, 3.5 mmol) was added. The mixture was cooled in an ice bath and HBTU (1.52 g, 4.0 mmol) was added. After 1 hour the ice bath was removed and the mixture was stirred overnight at room temperature. The mixture was evaporated in vacuo, redissolved in dichloromethane (100 mL) and washed with saturated aqueous NaHCO3 (2×50 mL). The organic phase was dried (MgSO4) and evaporated in vacuo. The crude product was purified on a silica column eluted with dichloromethane/methanol (97:3, v/v). Fractions containing the product were pooled and evaporated in vacuo to give 345 mg (21%) of the title compound as a tan solid.

後処理

  1. temperatureThe mixture was cooled in an ice bath
  2. customAfter 1 hour the ice bath was removed
  3. customThe mixture was evaporated in vacuo
  4. dissolutionredissolved in dichloromethane (100 mL)
  5. washwashed with saturated aqueous NaHCO3 (2×50 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated in vacuo
  8. customThe crude product was purified on a silica column
  9. washeluted with dichloromethane/methanol (97:3
  10. additionFractions containing the product
  11. customevaporated in vacuo

出典と根拠

ORDレコード
ord-b5b9b58ef8fe473d868c3b6f95adb4c7
出典データセット
uspto-grants-2003_10
特許番号
US06632919B1

反応ノート

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