P-Phenylenediamine → [4-(4-Amino-phenylcarbamoyl)-benzyl]-carbamic acid tert-butyl ester

HRID 19616

Reaction equation

HRID 19616 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=1>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:41][C:42]2[CH:47]=[CH:46][C:45]([NH2:48])=[CH:44][CH:43]=2)=[CH:17][CH:18]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 7814P-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67319189[4-(4-Amino-phenylcarbamoyl)-benzyl]-carbamic acid tert-butyl esterYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

To a solution of 4-(tert-butoxycarbonylamino-methyl)-benzoic acid (1.005 g) and N-hydroxy-benzotriazole (HOBt)(0.642 g) in DMF (30 ml) are added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC)(2.76 g) and triethylamine (2.005 ml). The mixture is stirred for 1 h at ambient temperature. This solution is added at 0° C. slowly to a solution of 1,4-diaminobenzene (0.43 g) and triethylamine (0.45 ml) in DMF (5 ml). After completion of the chemical reaction the mixture is evaporated at high vacuum and the residue is partitioned between ethyl acetate and an aqueous saturated sodium bicarbonate solution. The organic phase is dried over sodium sulfate and the crude product is purified by silica gel flash chromatography. A colorless solid (0.735 g) is obtained in 55% yield.

Workup

  1. customAfter completion of the chemical reaction the mixture
  2. customis evaporated at high vacuum
  3. customthe residue is partitioned between ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-8d3603ac7c024e62b278797a849ef08e
Source dataset
uspto-grants-2010_06
Patent number
US07745446B2

Linked notes

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