1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86595990, compound

HRID 1828986Notes

Reaction equation

HRID 1828986 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:29])[CH2:10][C:11]1[CH:28]=[CH:27][C:14]2[O:15][CH:16]([CH2:18][NH:19][C:20](=[O:26])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])[O:17][C:13]=2[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:31]1[C:35](=[O:36])[CH2:34][CH2:33][C:32]1=[O:37].C(N=C=NCCCN(C)C)C>ClCCl>[O:37]=[C:32]1[CH2:33][CH2:34][C:35](=[O:36])[N:31]1[O:24][C:23](=[O:25])[CH2:22][CH2:21][C:20]([NH:19][CH2:18][CH:16]1[O:15][C:14]2[CH:27]=[CH:28][C:11]([CH2:10][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:29])=[CH:12][C:13]=2[O:17]1)=[O:26]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 22061561HCID 22061561, compound

Product 1

HCID 86595990HCID 86595990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 32 mg (0.078 mmol) of 3G was added 4 mL of dichloromethane (distilled over CaH2) followed by 14 mg (0.12 mmol) of N-hydroxysuccinimide and 30 mg (0.152 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide. The reaction mixture was allowed to stir at room temperature under argon atmosphere 18 hours. The reaction mixture was diluted with additional 25 mL of dichloromethane and washed with 2×20 mL of water, 2×20 mL of saturated sodium bicarbonate and 1×20 mL of water. The organic layer was dried (Na2SO4) and concentrated to give 36 mg (0.071 mmol) of 3H as a colorless gum.

Workup

  1. washwashed with 2×20 mL of water, 2×20 mL of saturated sodium bicarbonate and 1×20 mL of water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give 36 mg (0.071 mmol) of 3H as a colorless gum

Sources & evidence

ORD record
ord-13ccf5e458a74caabbb67915917f1cab
Source dataset
uspto-grants-2006_06
Patent number
US07060847B2

Reaction notes

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