4-Iodoaniline → [2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester

HRID 254369노트

반응식

HRID 254369 반응식
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:13][C:14]([NH:16][CH2:17][CH2:18][C:19](O)=[O:20])=[O:15])([CH3:12])([CH3:11])[CH3:10].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1>CN(C=O)C>[C:9]([O:13][C:14](=[O:15])[NH:16][CH2:17][CH2:18][C:19](=[O:20])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)([CH3:12])([CH3:10])[CH3:11]

참가 물질

6

반응물 4

HCID 108934-IodoanilineHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 29404500[2-(4-Iodophenylcarbamoyl)ethyl]carbamic acid tert-butyl ester수율 73.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-iodoaniline (2.0 g, 9.17 mmol), 3-tert-butoxycarbonylaminopropionic acid (1.61 g, 8.49 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.95 g, 10.19 mmol), 1-hydroxy-7-azabenzotriazole (0.12 g, 0.85 mmol), and DMF (20 mL), was stirred at room temperature for 72 hours. The solvent was evaporated in vacuo. The residue was dissolved in methylene chloride (100 mL) and washed with 10% citric acid (2×50 mL), then 10% aqueous K2CO3 (2×50 mL). The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 3:1, v/v hexanes/ethyl acetate, then 1:1 hexanes/ethyl acetate) to provide 310 (2.44 g, 69%). 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 2.60 (t, 2H), 3.49 (q, 2H), 7.36 (d, 2H), 7.60 (d, 2H).

후처리

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride (100 mL)
  3. washwashed with 10% citric acid (2×50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (silica gel, 3:1, v/v hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-456a2631cf644dd993cc24cc677d09f5
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875619B2

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