1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58504202, compound

HRID 2407737Notes

Reaction equation

HRID 2407737 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]([CH:23]=[C:24]([O:26][CH2:27][CH3:28])[N:25]=2)[C:18]([O:20]CC)=O)C2C=CC=CC=2)C=CC=CC=1.O.[OH-].[Li+].[C:32]1([C:38]2[CH:42]=[C:41]([CH2:43][N:44]3[CH2:49][CH2:48][CH:47]([CH2:50][NH2:51])[CH2:46][CH2:45]3)[O:40][N:39]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C.O.ON1C2C=CC=CC=2N=N1>CO.ClCCl.O.O1CCCC1>[NH2:14][C:15]1[CH:16]=[C:17]([CH:23]=[C:24]([O:26][CH2:27][CH3:28])[N:25]=1)[C:18]([NH:51][CH2:50][CH:47]1[CH2:46][CH2:45][N:44]([CH2:43][C:41]2[O:40][N:39]=[C:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:42]=2)[CH2:49][CH2:48]1)=[O:20]

Participants

11

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 168937Lithium hydroxide, monohydrateHCID 27960291-Hydroxybenzotriazole hydrateHCID 58503960HCID 58503960, compoundHCID 58504252HCID 58504252, compound

Product 1

HCID 58504202HCID 58504202, compoundYield 22%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 230 (0.090 g) and lithium hydroxide hydrate (0.011 g) were combined in methanol (1 mL), tetrahydrofuran (1 mL) and water (0.1 mL) and allowed to stir for 48 hours. The reaction was concentrated, pumped to dryness and used without further purification. The crude acid was combined with the compound prepared in Example 9 (0.11 g, 0.31 mmol), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide (0.069 g, 0.36 mmol), diisopropylethylamine (0.16 g, 1.2 mmol) and 1-hydroxybenzotriazole hydrate (0.049 g, 0.36 mmol) in dichloromethane (2.5 mL). The reaction was sonicated briefly to aid dissolution and then stirred for 24 hours. The crude reaction was concentrated and then dissolved in methanol and treated with 2N hydrochloric acid. After stirring for 15 minutes, this solution was concentrated and then partitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution. The organic phase was dried over magnesium sulfate, filtered, concentrated and purified by column chromatography using an eluant of 4% methanol/dichloromethane to provide the title compound (0.023 g) with the following physical data.

Workup

  1. concentrationThe reaction was concentrated
  2. customused without further purification
  3. customThe reaction was sonicated briefly
  4. dissolutiondissolution
  5. stirringstirred for 24 hours
  6. customThe crude reaction
  7. concentrationwas concentrated
  8. dissolutiondissolved in methanol
  9. additiontreated with 2N hydrochloric acid
  10. stirringAfter stirring for 15 minutes
  11. concentrationthis solution was concentrated
  12. custompartitioned between ethyl acetate and sodium hydrogen carbonate aqueous solution
  13. dry with materialThe organic phase was dried over magnesium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. custompurified by column chromatography

Sources & evidence

ORD record
ord-72462de62e0d418ba70e17f11843968e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

Loading…