1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500673, compound

HRID 632961Notes

Reaction equation

HRID 632961 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.[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]1[O:44][C:45]([CH3:51])=[C:46]([C:48](O)=[O:49])[N:47]=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:48]([C:46]3[N:47]=[C:43]([C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=4[Cl:36])[O:44][C:45]=3[CH3:51])=[O:49])=[CH:16][CH:17]=2)[CH2:10][CH2:11]1

Participants

8

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 62235403HCID 62235403, compoundHCID 178500667HCID 178500667, compound

Product 1

HCID 178500673HCID 178500673, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-{4-[4-(3-aminopropionylamino)-phenyl]cyclohexyl}acetic acid methyl ester HCl salt (60 mg, 0.169 mmol), EDCI (81.05 mg, 0.423 mmol), 2-(2-chloro-phenyl)-5-methyl-oxazole-4-carboxylic acid (44.2 mg, 0.186 mmol), HOBt (34.28 mg, 0.254 mmol) and ethyldiisopropylamine (76.68 mg, 0.592 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. Column chromatography was conducted on the crude material to obtain trans-{4-[4-(3-{[2-(2-chlorophenyl)-5-methyloxazole-4-carbonyl]amino}propionylamino)phenyl]cyclohexyl}acetic acid methyl ester (80 mg, 88%).

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-017a45d3204a4c09b70431407db4368a
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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