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

HRID 19616

반응식

HRID 19616 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8d3603ac7c024e62b278797a849ef08e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745446B2

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