1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68002031, compound

HRID 2046024Notes

Reaction equation

HRID 2046024 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].O[NH:17][C:18]([C:20]1[CH:21]=[CH:22][C:23]2[O:27][C:26]([CH2:28][OH:29])=[CH:25][C:24]=2[CH:30]=1)=[NH:19].[CH2:31](N=C=NCCCN(C)C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CS(C)=O.O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:19]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]4[O:27][C:26]([CH:28]([OH:29])[CH3:31])=[CH:25][C:24]=4[CH:30]=3)[N:17]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 794173,4-Diethoxybenzoic acidHCID 2724141Tetrabutylammonium FluorideHCID 178513244HCID 178513244, compound

Product 1

HCID 68002031HCID 68002031, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-diethoxybenzoic acid (0.21 g; 1 mmol), the product of Step C (0.2 g; 0.97 mmol) and hydrochloride salt of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) (0.22 g; 1.15 mmol) in anhydrous dimethylsulfoxide (DMSO) (2 ml) was stirred for 20 min at ˜40° C. under N2. To it 1M tetra-n-butylammonium fluoride (TBAF) in terahydrofuran (THF) (0.4 ml) was added and the resulting mixture was stirred for 1 h at ˜120° C., then overnight at room temperature. The solvents were removed in vacuo and the residue was partitioned between EtOAc (15 ml) and H2O (5 ml). The organic phase was washed with brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2) to give the title compound (0.13 g; 34%), as greyish solid. 1H-NMR (CDCl3) 8.36 (d, 1H, J=3 Hz); 8.09 (dd, 1H, J=3, 9 Hz); 7.79 (dd, 1H, J=3, 9 Hz); 7.68 (d, 1H, J=3 Hz); 7.55 (d, 1H, J=9 Hz); 6.98 (d, 1H, J=9 Hz); 6.73 (s, 1H); 4.8 (s, 2H); 4.2 (m, 4H); 2.02 (s, 1H); 1.51 (m, 6H);

Workup

  1. customovernight
  2. customat room temperature
  3. customThe solvents were removed in vacuo
  4. customthe residue was partitioned between EtOAc (15 ml) and H2O (5 ml)
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness under reduced pressure
  9. customthe residue was purified by FCC (SiO2; CH2Cl2)

Sources & evidence

ORD record
ord-c943cc08f0004dd7830cb59db59f2404
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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