1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178472069, compound

HRID 1633894Notes

Reaction equation

HRID 1633894 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([CH:11]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=2)=[O:23])[C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.Cl.[CH2:67]([O:69][C:70](=[O:74])[CH2:71][CH2:72][NH2:73])[CH3:68]>CN(C=O)C.O.C(OCC)(=O)C>[CH2:67]([O:69][C:70](=[O:74])[CH2:71][CH2:72][NH:73][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:12]([CH:11]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]([F:34])([F:35])[F:33])=[CH:27][CH:26]=2)=[O:23])[C@H:8]2[CH2:9][CH2:10][C@@H:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:6][CH2:7]2)=[CH:13][CH:14]=1)[CH3:68]

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 178445644HCID 178445644, compound

Product 1

HCID 178472069HCID 178472069, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-[1-(cis-4-tert-Butylcyclohexyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acid (0.3 g, 0.6 mmol), 1-hydroxybenzotriazole (0.1 g, 0.7 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.13 g, 0.7 mmol) were dissolved in DMF (10 mL). Diisopropylethylamine (0.1 g, 0.7 mmol) and 3-aminopropionic acid ethyl ester, hydrochloride (0.07 g, 0.7 mmol) in DMF was added and the reaction mixture was stirred for 16 hours at 20° C. Ethyl acetate (80 mL) and water (50 mL) were added and the organic phase isolated. The aqueous phase was extracted with ethyl acetate (50 mL) and the organic phases combined, dried (MgSO4) and concentrated in vacuo. The residue was crystallised from heptane and ethyl acetate (4:1) to give 3-{4-[1-(cis-4-tert-butylcyclohexyl)-3-(4-trifluoromethoxy-phenyl)ureidomethyl]benzoylamino}propionic acid ethyl ester.

Workup

  1. customthe organic phase isolated
  2. extractionThe aqueous phase was extracted with ethyl acetate (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallised from heptane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-989720d0d60b4c76961259b42db04366
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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