1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178472070, compound

HRID 1633893Notes

Reaction equation

HRID 1633893 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 178445645HCID 178445645, compound

Product 1

HCID 178472070HCID 178472070, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

4-[1-(trans-4-tert-Butylcyclohexyl)-3-(4-trifluoromethoxyphenyl)ureidomethyl]benzoic acid (2.0 g, 4.1 mmol), 1-hydroxybenzotriazole (0.6 g, 4.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (0.8 g, 4.3 mmol) were dissolved in DMF (40 mL). A solution of diisopropylethylamine (0.5 g, 4.1 mmol) and 3-aminopropionic acid ethyl ester, hydrochloride (0.4 g, 4.3 mmol) in DMF (10 mL) was added and the reaction mixture was stirred for 16 hours at 20° C. Ethyl acetate (150 mL) and water (100 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 crude product was purified on silica (80 g) using heptane and ethyl acetate (1:1) as eluent to give 3-{4-[1-(trans-4-tert -butylcyclohexyl)-3-(4-trifluoromethoxyphenyl)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 crude product was purified on silica (80 g)

Sources & evidence

ORD record
ord-7b7e3faf823345ad87093ad4a916c902
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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