Triethylamine → HCID 10075034, compound

HRID 131629Notes

Reaction equation

HRID 131629 reaction equation
C[C:2]1[C:6]([CH2:7][C:8]2[S:23][C:11]3[N:12]([CH2:19][CH:20](C)C)[C:13](=[O:18])[N:14]([CH3:17])[C:15](=[O:16])[C:10]=3[C:9]=2[C:24]([N:26]2[CH2:30][C@:29]([CH3:32])([OH:31])[CH2:28][O:27]2)=[O:25])=[C:5](C)NN=1.ON1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[N:37]=[N:36]1.[CH2:44](N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>ClCCl.O>[OH:31][C@:29]1([CH3:32])[CH2:28][O:27][N:26]([C:24]([C:9]2[C:10]3[C:15](=[O:16])[N:14]([CH3:17])[C:13](=[O:18])[N:12]([CH:19]([CH3:44])[CH3:20])[C:11]=3[S:23][C:8]=2[CH2:7][C:6]2[CH:5]=[N:36][N:37]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:2]=2)=[O:25])[CH2:30]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9982392HCID 9982392, compound

Product 1

HCID 10075034HCID 10075034, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of part c) (0.5 g), the product of example 1 part d) (0.18 g), and 1-hydroxybenzotriazole (0.36 g) in dichloromethane (10 ml) was added triethylamine (0.36 ml) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.45 g) and the mixture stirred at ambient temperature under nitrogen for 18 hr. It was diluted with water and extracted with dichloromethane, the organic extracts were washed successively with 1.0N sodium hydroxide and water, dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with ethyl acetate/methanol (99:1) followed by ethyl acetate/methanol (49:1) to give the title compound as a solid (0.14 g).

Workup

  1. extractionextracted with dichloromethane
  2. washthe organic extracts were washed successively with 1.0N sodium hydroxide and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography over silica
  7. washeluting with ethyl acetate/methanol (99:1)

Sources & evidence

ORD record
ord-87dc1fd8ac224ec7889462502d422e96
Source dataset
uspto-grants-2008_06
Patent number
US07384951B2

Reaction notes

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