1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178500677, compound

HRID 632935Notes

Reaction equation

HRID 632935 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.CCN=C=NCCCN(C)C.[C:30]1([C:36]2[O:37][C:38]([C:49]([F:52])([F:51])[F:50])=[C:39]([C:41]([NH:43][CH2:44][CH2:45][C:46](O)=[O:47])=[O:42])[N:40]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)C(C)C)C>ClCCl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]2[CH:12]=[CH:13][C:14]([NH:17][C:46](=[O:47])[CH2:45][CH2:44][NH:43][C:41]([C:39]3[N:40]=[C:36]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[O:37][C:38]=3[C:49]([F:51])([F:52])[F:50])=[O:42])=[CH:15][CH:16]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1179201883-[(2-Phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acidHCID 178500653HCID 178500653, compound

Product 1

HCID 178500677HCID 178500677, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Trans-[4-(4-aminophenyl)cyclohexyl]acetic acid methyl ester (150 mg, 0.6 mmol), EDCI (290.7 mg, 1.5 mmol), 3-[(2-phenyl-5-trifluoromethyloxazole-4-carbonyl)amino]propionic acid (228.9 mg, 0.7 mmol), HOBt (123 mg, 0.91 mmol) and ethyldiisopropylamine (275 mg, 0.21 mmol) dissolved in dichloromethane (15 mL) were stirred for 24 hours. The reaction mixture was diluted with aqueous NaHCO3 and extracted with dichloromethane. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the desired compound (330 mg, 98%) as a white solid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract was washed with brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-16c12df558834f9b9e09570854efdfa3
Source dataset
uspto-grants-2016_04
Patent number
US09321728B2

Reaction notes

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