1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69592241, compound

HRID 2213691Notes

Reaction equation

HRID 2213691 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:15]([NH2:16])[C@@H:14]2[CH2:17][C@H:11]1[CH2:12][CH2:13]2.[N:19]1([S:24]([C:27]2[S:31][C:30]([C:32](O)=[O:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20]1.ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C>O1CCCC1.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:15]([NH:16][C:32]([C:30]2[S:31][C:27]([S:24]([N:19]3[CH:23]=[CH:22][CH:21]=[CH:20]3)(=[O:26])=[O:25])=[CH:28][CH:29]=2)=[O:33])[C@@H:14]2[CH2:17][C@H:11]1[CH2:12][CH2:13]2

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 14134677HCID 14134677, compoundHCID 22016842HCID 22016842, compound

Product 1

HCID 69592241HCID 69592241, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 251 mg (1.0 mmol) of (5Z)-7-[(1R,2S,3S,4S)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid methyl ester (1) in 4 ml of tetrahydrofuran were added 257 mg (1.0 mmol) of 5 -(pyrrol-1-ylsulfonyl)thiophen-2-carboxylic acid and 13.5 mg (0.1 mmol) of 1-hydroxybenzotriazole. Under ice-cooling, 186 mg (1.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide was added thereto. The mixture was warmed to room temperature and stirred at 25° C. for 16 h. The mixture was diluted with water and extracted with toluene. The organic layer was washed with dilute hydrochloric acid and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel (toluene/ethyl acetate=6:1) to give 412 mg of (5Z)-7-{(1R,2S,3S,4S)-3-[5-(pyrrol-1-ylsulfonyl)-thiophen-2-ylcarbonylamino]-bicyclo[2.2.1]hept-2-yl}-5-heptenoic acid methyl ester (I-la). Yield 83.9%.

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted with toluene
  3. washThe organic layer was washed with dilute hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel (toluene/ethyl acetate=6:1)

Sources & evidence

ORD record
ord-bc9c1752196242688851bed874f08fa7
Source dataset
uspto-grants-2006_09
Patent number
US07105564B1

Reaction notes

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