1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoyl-amino}propionic acid methyl ester

HRID 49547Notes

Reaction equation

HRID 49547 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:35])[N:12]([CH2:25][C:26]2[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=2)[C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[CH3:9])=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:58][O:59][C:60](=[O:64])[CH2:61][CH2:62][NH2:63].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:58][O:59][C:60](=[O:64])[CH2:61][CH2:62][NH:63][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][C:26]([CH2:25][N:12]([C:13]2[CH:14]=[CH:15][C:16]([CH:19]3[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]3)=[CH:17][CH:18]=2)[C:11]([NH:10][C@H:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:9])=[O:35])=[CH:27][CH:28]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 674838354-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid

Product 1

HCID 674838893-{4-[3-[1(S)-(4-Chlorophenyl)ethyl]-1-(4-cyclohexylphenyl)ureidomethyl]benzoyl-amino}propionic acid methyl esterYield 99.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-[3-[1(S)-(4-Chlorophenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoic acid (1.0 g, 2.04 mmol) was dissolved in DMF (8 ml) and HOBt (410 mg, 3.05 mmol), and EDAC (580 mg, 3.05 mmol) were added. The solution was stirred at room temperature for 30 min. A solution of 3-aminopropionic acid methyl ester hydrochloride (310 mg, 3.05 mmol) and N,N-diisopropylethylamine (530 μl, 3 mmol) in DMF (2 ml) was added, and the reaction mixture was stirred at ambient temperature over night. The reaction mixture was partitioned between ethyl acetate (70 ml) and water (3×50 ml). The organic phase was dried with anhydrous sodium sulfate and evaporated to dryness to afford 1.17 g (99%) of 3-{4-[3-[1(S)-(4-chloro-phenyl)ethyl]1-(4-cyclohexylphenyl)ureidomethyl]benzoylamino}propionic acid methyl ester. HPLC-MS (method A): m/z=576 (M+1); Rt=5.47 min.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature over night
  2. customThe reaction mixture was partitioned between ethyl acetate (70 ml) and water (3×50 ml)
  3. dry with materialThe organic phase was dried with anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a1be2e6f80c946bea94530a0ffc9ecfc
Source dataset
uspto-grants-2004_03
Patent number
US06706744B2

Reaction notes

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