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

HRID 254369Notes

Reaction equation

HRID 254369 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-456a2631cf644dd993cc24cc677d09f5
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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