Cyclopentanol → Ethyl 4-(t-butoxycarbonylamino)-2-cyclopentyloxybenzoate

HRID 49944

반응식

HRID 49944 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([OH:20])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:21]1(O)[CH2:25][CH2:24][CH2:23][CH2:22]1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:10]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 17834349Ethyl 4-(t-Butoxycarbonylamino)-2-hydroxybenzoate

생성물 1

HCID 17834381Ethyl 4-(t-butoxycarbonylamino)-2-cyclopentyloxybenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 460 mg of ethyl 4-(t-butoxycarbonylamino)-2-hydroxybenzoate, 300 mg of cyclopentanol, 1.5 g of diethyl azodicarboxylate (40% solution in toluene), 900 mg of triphenylphosphine and 10 ml of tetrahydrofuran was stirred at room temperature for 3 days. The solvent was evaporated and the residue was purified by the silica gel chromatography (ethyl acetate/hexane) to obtain crude ethyl 4-(t-butoxycarbonylamino)-2-cyclopentyloxybenzoate. A mixture of this crude product, 20 ml of ethanol and 5 ml of 1 M aqueous sodium hydroxide solution was stirred at room temperature overnight. After the treatment with ethyl acetate as the extracting solvent in an ordinary manner, the title compound was obtained.

후처리

  1. customThe solvent was evaporated
  2. customthe residue was purified by the silica gel chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-abec80d2a00946b3ba38919b8e07f98f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710056B2

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