1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 66631721, compound

HRID 405023Notes

Reaction equation

HRID 405023 reaction equation
C(OC(=O)C([NH:16][C:17](=[O:32])[C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:20][CH:19]=1)CC1C=CC(C#N)=C(F)C=1)C.CCN=C=NCCCN(C)C.[C:45]([O:49][C:50]([NH:52][C:53]1[CH:61]=[CH:60][C:56]([C:57]([OH:59])=O)=[CH:55][CH:54]=1)=[O:51])([CH3:48])([CH3:47])[CH3:46].C([O:64][C:65](=[O:78])[CH:66]([NH2:77])[CH2:67][C:68]1[CH:73]=[CH:72][C:71]([C:74]#[N:75])=[C:70]([F:76])[CH:69]=1)C>C(Cl)Cl>[C:45]([O:49][C:50]([NH:52][C:53]1[CH:54]=[CH:55][C:56]([C:57]([NH:77][CH:66]([CH2:67][C:68]2[CH:73]=[CH:72][C:71]([C:74]3[N:16]=[C:17]([C:18]4[CH:19]=[CH:20][C:21]([NH:24][C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[CH:22][CH:23]=4)[O:32][N:75]=3)=[C:70]([F:76])[CH:69]=2)[C:65]([OH:78])=[O:64])=[O:59])=[CH:60][CH:61]=1)=[O:51])([CH3:46])([CH3:47])[CH3:48]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acidHCID 66630098HCID 66630098, compoundHCID 66630753HCID 66630753, compound

Product 1

HCID 66631721HCID 66631721, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(4-tert-Butoxycarbonylamino-benzoylamino)-3-(4-cyano-3-fluoro-phenyl)-propionic acid ethyl ester. EDCI (560 mg, 2.92 mmol) was added to a solution of 4-tert-butoxycarbonylamino-benzoic acid (661 mg, 2.7 mmol) in dry CH2Cl2 (5 mL). After the mixture was stirred for 0.5 hr, 2-amino-3-(4-cyano-3-fluoro-phenyl)-propionic acid ethyl ester (627 mg, 2.66 mmol) was added and the mixture was stirred for another 5 hrs at room temperature. The mixture was partitioned between EtOAc and water. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated under reduced pressure, and purified by silica gel chromatography to give the title compound as a white solid (906 mg, 75% yield).

Workup

  1. stirringthe mixture was stirred for another 5 hrs at room temperature
  2. customThe mixture was partitioned between EtOAc and water
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f775d40f497048e3ba929a6d15602fd1
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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