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

HRID 49944

Reaction equation

HRID 49944 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-abec80d2a00946b3ba38919b8e07f98f
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Linked notes

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