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

HRID 49944

反応式

HRID 49944 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-abec80d2a00946b3ba38919b8e07f98f
出典データセット
uspto-grants-2004_03
特許番号
US06710056B2

関連ノート

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