1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-3{-4-[1-(4-Cyclohex-1-enylphenyl)-3-(3,5-dichlorophenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid

HRID 412444Notes

Reaction equation

HRID 412444 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)=[O:25])[C:14]3[CH:22]=[CH:21][C:17](C(O)=O)=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.FC(F)(F)[C:58]([O-])=[O:59].CC1(C)[O:68][C@@H:67]([CH2:69][NH3+:70])[C:66](=[O:71])[O:65]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)=[O:25])[C:14]3[CH:22]=[CH:21][C:17]([C:58]([NH:70][CH2:69][C@H:67]([OH:68])[C:66]([OH:65])=[O:71])=[O:59])=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 223110574-[1-(4-Cyclohex-1-enylphenyl)-3-(3,5-dichlorophenyl)ureidomethyl]benzoic acidHCID 86586053(S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethylammonium trifluoroacetate

Product 1

HCID 67485046(S)-3{-4-[1-(4-Cyclohex-1-enylphenyl)-3-(3,5-dichlorophenyl)ureidomethyl]benzoylamino}-2-hydroxypropionic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4-[1-(4-Cyclohex-1-enylphenyl)-3-(3,5-dichlorophenyl)ureidomethyl]benzoic acid (130 mg, 0.26 mmol) was dissolved in DMF (2 mL), then EDAC (50 mg, 0.26 mmol) and HOBt (43 mg, 0.32 mmol) were added and the reaction mixture was stirred at room temperature for 1 hour. The above crude (S)-2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylmethylammonium trifluoroacetate was dissolved in DMF (1 mL) and added to the reaction mixture together with diisopropylethylamine (450 mg, 3.5 mmol). The mixture was stirred at room temperature for 16 hours.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours

Sources & evidence

ORD record
ord-02ebf157de16404fbabea289291e79d0
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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