Benzoic Acid → [(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoate

HRID 1455583노트

반응식

HRID 1455583 반응식
[C:1]([O:5][C:6](=[O:17])[NH:7][C@H:8]([CH:11]([OH:16])[C:12](=[NH:15])[NH:13][OH:14])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].[C:18](O)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([CH:11]([OH:16])[C:12](=[NH:15])[NH:13][O:14][C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 243Benzoic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 178456097HCID 178456097, 화합물

생성물 1

HCID 178458006[(Z)-[1-amino-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]pentylidene]amino] benzoate수율 24.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of {1-[hydroxy-(N-hydroxycarbamimidoyl)-methyl]-propyl}-carbamic acid tert-butyl ester (2) (2.5 g, 10 mmol) in dichloromethane (125 mL) is treated with benzoic acid (1.36 g, 11 mmol), EDCI (2.14 g, 11 mmol), HOBT (1.37 g, 10 mmol) and triethylamine (1.35 mL, 11 mmol) and stirred at room temperature overnight. The reaction mixture is washed with saturated sodium bicarbonate solution, then water, then dried over Na2SO4 and then evaporated under reduced pressure. The residue is subjected to mplc eluting with 1% triethylamine in 2:3 v/v ethyl acetate and heptane mixture to give {1-[hydroxy-(N-benzoyloxycarbamimidoyl)-methyl]-propyl}-carbamicacid tert-butyl ester (850 mg) as a solid. MS: MH+ 352.

후처리

  1. washThe reaction mixture is washed with saturated sodium bicarbonate solution
  2. dry with materialwater, then dried over Na2SO4
  3. customevaporated under reduced pressure
  4. washto mplc eluting with 1% triethylamine in 2:3 v/v ethyl acetate and heptane mixture

출처 및 근거

ORD 기록
ord-9c553974e47346d6809cae465289ed5b
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482448B2

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