1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18508351, compound

HRID 1356455Notes

Reaction equation

HRID 1356455 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:43][NH:44][CH2:45][CH2:46][N:47]([CH3:49])[CH3:48]>C1COCC1.C(N(CC)CC)C>[CH3:48][N:47]([CH3:49])[CH2:46][CH2:45][N:44]([CH3:43])[C:19](=[O:21])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 757711-HydroxybenzotriazoleHCID 21939874HCID 21939874, compound

Product 1

HCID 18508351HCID 18508351, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of (4-(((benzyloxy)carbonyl)amino)-phenyl)acetic acid (6 g) in THF (100 ml) were added WSC (4 G), HOBt (3 g), and N,N,N-trimethylethylenediamine (2.1 g) sequentially. Triethylamine (3 ml) was added to the reaction mixture. After stirring at room temperature overnight, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated. The residue was recrystallized from IPE/ethyl acetate to obtain the titled compound (7 g).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from IPE/ethyl acetate

Sources & evidence

ORD record
ord-1b8c4551f27e433e925c267828eabf4a
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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