Ethanol → Ethyl 4-(t-Butoxycarbonylamino)-2-hydroxybenzoate

HRID 49943

Reaction equation

HRID 49943 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[C:11]([OH:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)[CH2:22][CH2:23]CN=C=NCC.C(O)C>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([O:15][CH2:22][CH3:23])=[O:14])=[C:11]([OH:18])[CH:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103324764-(((Tert-butoxy)carbonyl)amino)-2-hydroxybenzoic acid

Product 1

HCID 17834349Ethyl 4-(t-Butoxycarbonylamino)-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.2 g of 4-(t-butoxycarbonylamino)-2-hydroxybenzoic acid, 900 mg of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (WSC·HCl), 550 mg of 4-dimethylaminopyridine, 1 ml of ethanol and 30 ml of dichloromethane was stirred at room temperature. The reaction mixture was treated with dichloromethane as the extracting solvent in an ordinary manner and then purified by the silica gel chromatography (ethyl acetate/hexane) to obtain the title compound.

Workup

  1. custompurified by the silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6ad0c6b22fd34371956974c9cbee2ff2
Source dataset
uspto-grants-2004_03
Patent number
US06710056B2

Linked notes

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