1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178482544, compound

HRID 493723Notes

Reaction equation

HRID 493723 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][C@@H:16]([OH:20])[C:17]([OH:19])=O)(=[O:14])=[O:13])[CH:6]=[CH:5]2.Cl.Cl.Cl.[CH3:24][N:25]1[C:29]([CH2:30][N:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)=[CH:28][S:27]/[C:26]/1=[N:37]\[CH3:38].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([CH2:15][C@@H:16]([OH:20])[C:17]([N:34]1[CH2:35][CH2:36][N:31]([CH2:30][C:29]3[N:25]([CH3:24])/[C:26](=[N:37]/[CH3:38])/[S:27][CH:28]=3)[CH2:32][CH2:33]1)=[O:19])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66854329(2S)-3-[(6-chloro-2-naphthyl)sulfonyl]-2-hydroxypropionic acidHCID 178482538HCID 178482538, compound

Product 1

HCID 178482544HCID 178482544, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of (2S)-3-((6-chloronaphthalen-2-yl)sulfonyl)-2-hydroxypropanoic acid (0.32 g), N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride (0.51 g), HOBt (0.20 g) and triethylamine (0.63 mL) in DMF (5 mL), WSC (0.21 g) was added, and the mixture was mixed at room temperature for 22 hours. The reaction solution was concentrated under reduced pressure. The residue was basified with an aqueous potassium carbonate solution, and then the mixture was extracted with ethyl acetate/THF. The extract was dried over anhydrous magnesium sulfate, the solvent was then distilled off, and the residue was purified with a basic silica gel column to give the title compound (0.12 g, 23%) as a colorless powder.

Workup

  1. additionwas added
  2. additionthe mixture was mixed at room temperature for 22 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. extractionthe mixture was extracted with ethyl acetate/THF
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was then distilled off
  7. customthe residue was purified with a basic silica gel column

Sources & evidence

ORD record
ord-231f28a1636847148b731fcb15cb9243
Source dataset
uspto-grants-2009_05
Patent number
US07534887B2

Reaction notes

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