HOAt → Tert-butyl 2-(aminocarbonyl)-4-fluorobenzylcarbamate

HRID 2252815ノート

反応式

HRID 2252815 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:11]=1[C:12](O)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:22](C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C=O)C>[NH2:22][C:12]([C:11]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:10]=1[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:13]

参加物

5

反応物 3

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110654742-[[(tert-Butoxycarbonyl)amino]methyl]-5-fluorobenzoic acid

生成物 1

HCID 59645228Tert-butyl 2-(aminocarbonyl)-4-fluorobenzylcarbamate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-{[(Tert-butoxycarbonyl)amino]methyl}-5-fluorobenzoic acid (800 mg, 2.97 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (854 mg, 4.46 mmol), and 1-hydroxy-7-azabenzotriazole (607 mg, 4.46 mmol) were added to dry DMF (10 mL) and stirred for 30 minutes to preform the activated ester. Ammonia gas was bubbled through the solution for 30 seconds and the reaction was allowed to stir for 5 minutes. The solvent was removed in vacuo and the residue was purified by flash column chromatography (ISCO column, 120 g silica) running a gradient of 0-40% acetone/hexane over 35 min. The product fractions were concentrated to afford the title compound as a white solid.

後処理

  1. customAmmonia gas was bubbled through the solution for 30 seconds
  2. stirringto stir for 5 minutes
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash column chromatography (ISCO column, 120 g silica)
  5. customover 35 min
  6. concentrationThe product fractions were concentrated

出典と根拠

ORDレコード
ord-90de591c052c438e96e669424661f1cd
出典データセット
uspto-grants-2008_01
特許番号
US07323460B2

反応ノート

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