1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59548531, compound

HRID 1879670

Reaction equation

HRID 1879670 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[CH2:26]([O:28][CH:29]([O:32][CH2:33][CH3:34])[CH2:30][NH2:31])[CH3:27].CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1>C1COCC1.O>[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]([NH:31][CH2:30][CH:29]([O:32][CH2:33][CH3:34])[O:28][CH2:26][CH3:27])=[O:8])([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 695242,2-DiethoxyethylamineHCID 81531DiisopropylethylamineHCID 2573264-Tert-butyl-2-nitrobenzoic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 59548531HCID 59548531, compoundYield 40.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-nitro-4-tert-butylbenzoic acid (1.5 g, 7 mmol, prepared according to J. Am. Chem. Soc, 1955, 77, 5441) was stirred in THF at room temperature, 1.7 mL diisopropylethyl amine (13 mmol, 2 eq) was added, followed by 984 mg (7.7 mmol, 1.1 eq) 2-amino acetaldehyde diethylacetal. (3-Dimethylamino-propyl)-ethyl-carbodiimide (1.55 g, 8 mmol, 1.2 eq) was added, followed by a catalytic amount (ca. 50 mgs) hydroxybenzotriazole hydrate. The mixture was stirred at room temperature for 16 hours, diluted with water, extracted with diethyl ether 3×, the ether layers were washed with water, brine, and dried over MgSO4. Removal of solvent under vacuum, followed by chromatography on silica gel, eluting with 25% ethyl acetate in hexanes, gave the title compound 0.950 g, (M+H)+=224.

Workup

  1. extractionextracted with diethyl ether 3×
  2. washthe ether layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. customRemoval of solvent under vacuum
  5. washeluting with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-3ffc9684a3b04f1aae46226650e0c184
Source dataset
uspto-grants-2012_11
Patent number
US08318719B2

Linked notes

Loading…