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

HRID 405025Notes

Reaction equation

HRID 405025 reaction equation
C(OC(=O)C(NC(=O)C1C=CC(NC(OC(C)(C)C)=O)=CC=1)CC1C=CC(C2N=C(C3C=CC(NC(OC(C)(C)C)=O)=CC=3)ON=2)=CC=1F)C.CCN=C=NCCCN(C)C.[C:62]([O:66][C:67]([NH:69][C:70]1[CH:78]=[CH:77][C:73]([C:74](O)=[O:75])=[CH:72][CH:71]=1)=[O:68])([CH3:65])([CH3:64])[CH3:63].C([O:81][C:82](=[O:113])[CH:83]([NH:96][C:97](=[O:112])[C:98]1[CH:103]=[CH:102][C:101]([NH:104][C:105]([O:107][C:108]([CH3:111])([CH3:110])[CH3:109])=[O:106])=[CH:100][CH:99]=1)[CH2:84][C:85]1[CH:90]=[CH:89][C:88]([C:91](=[NH:94])[NH:92]O)=[C:87]([F:95])[CH:86]=1)C>C(Cl)Cl>[C:108]([O:107][C:105]([NH:104][C:101]1[CH:102]=[CH:103][C:98]([C:97]([NH:96][CH:83]([CH2:84][C:85]2[CH:90]=[CH:89][C:88]([C:91]3[N:94]=[C:74]([C:73]4[CH:77]=[CH:78][C:70]([NH:69][C:67]([O:66][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:68])=[CH:71][CH:72]=4)[O:75][N:92]=3)=[C:87]([F:95])[CH:86]=2)[C:82]([OH:113])=[O:81])=[O:112])=[CH:99][CH:100]=1)=[O:106])([CH3:111])([CH3:109])[CH3:110]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27559314-{[(Tert-butoxy)carbonyl]amino}benzoic acidHCID 66631174HCID 66631174, compoundHCID 178470926HCID 178470926, compound

Product 1

HCID 66631721HCID 66631721, compoundYield 9.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-(4-tert-Butoxycarbonylamino-benzoylamino)-3-{4-[5-(4-tert-butoxycarbonylamino-phenyl)-[1,2,4]oxadiazol-3-yl]-2-fluoro-phenyl}-propionic acid ethyl ester. EDCI (10 mg, 0.05 mmol) was added to a solution of 4-tert-butoxycarbonylamino-benzoic acid (12 mg, 0.05 mmol) in dry CH2Cl2 (5 mL). After the mixture was stirred for 0.5 hrs, 2-(4-tert-butoxycarbonylamino-benzoylamino)-3-[3-fluoro-4-(N-hydroxycarbamimidoyl)-phenyl]-propionic acid ethyl ester (25 mg) was added and the mixture was heated for another 1 hr at 120° C. in a sealed tube. 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 (3 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-743c91621b55463ba130fc57ab4b7d3a
Source dataset
uspto-grants-2014_06
Patent number
US08748412B2

Reaction notes

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