1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500669, compound

HRID 632963Notes

Reaction equation

HRID 632963 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.CCN=C=NCCCN(C)C.[C:36]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=[CH:40][C:39]([C:42](O)=[O:43])=[CH:38][CH:37]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C.C([O-])(O)=O.[Na+]>ClCCl>[CH3:2][O:3][C:4](=[O:24])[CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:23])[CH2:20][CH2:21][NH:22][C:42]([C:39]3[CH:40]=[CH:41][C:36]([C:45]4[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=4)=[CH:37][CH:38]=3)=[O:43])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 178500667HCID 178500667, compound

Product 1

HCID 178500669HCID 178500669, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-{4-[4-(3-aminopropionylamino)phenyl]cyclohexyl}acetic acid methyl ester HCl salt (50 mg, 0.141 mmol), EDCI (67.54 mg, 0.352 mmol), biphenyl-4-carboxylic acid (30.73 mg, 0.155 mmol), HOBt (28.56 mg, 0.211 mmol) and ethyldiisopropylamine (63.90 mg, 0.493 mmol) were put into dichloromethane solvent (10 mL) and stirred at room temperature for 24 hours. After the reaction, aqueous NaHCO3 was added thereto, and extracted with dichloromethane. The organic layer was washed with brine, then the product was dried with anhydrous sodium sulfate, and the solvent was removed. A column chromatography was conducted on the crude material to obtain trans-[4-(4-{3-[(biphenyl-4-carbonyl)-amino]-propionylamino}-phenyl)-cyclohexyl]-acetic acid methyl ester (64 mg, 91%).

Workup

  1. additionwas added
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialthe product was dried with anhydrous sodium sulfate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-e8b76c1dc762469486fea0fedc5ec7d0
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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