1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67208776, compound

HRID 70834Notes

Reaction equation

HRID 70834 reaction equation
CCN=C=NCCCN(C)C.ON1C2N=CC=CC=2N=N1.[CH2:22]([O:29][C:30](=[O:40])[CH2:31][C:32]1([C:37]([OH:39])=O)[CH2:36][CH2:35][CH2:34][CH2:33]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OC(C1(CC(O)=O)CCCC1)=O)C1C=CC=CC=1.Cl.[C:61]([O:65][C:66](=[O:83])[CH2:67][CH:68]([NH2:82])[CH2:69][C:70]1[CH:75]=[CH:74][C:73]([C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)=[CH:72][CH:71]=1)([CH3:64])([CH3:63])[CH3:62].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:22]([O:29][C:30](=[O:40])[CH2:31][C:32]1([C:37]([NH:82][CH:68]([CH2:69][C:70]2[CH:75]=[CH:74][C:73]([C:76]3[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=3)=[CH:72][CH:71]=2)[CH2:67][C:66]([O:65][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:83])=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 216902921-Carboxymethyl-cyclopentanecarboxylic acid benzyl esterHCID 596082261-(2-(Benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acidHCID 67208761HCID 67208761, compound

Product 1

HCID 67208776HCID 67208776, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Next, to a solution of EDCI (51.2 mg, 0.267 mmol), 1-hydroxy-7-azabenzotriazole (36.4 mg, 0.267 mmol) and 6:1 mixture of 1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxylic acid and 2-(1-(benzyloxycarbonyl)cyclopentyl)acetic acid (65.6 mg, 0.214 mmol) in DMF (1 ml), which is stirred for 1.5 hours in advance, the crude 3-amino-4-biphenyl-4-yl-butyric acid tert-butyl ester hydrochloride and DIPEA (0.093 ml, 0.535 mmol) are added. After stirring for 2.5 hours, the reaction mixture is diluted with H2O, and the products are extracted with EtOAc. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated. The obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 0:100) to give crude tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-4-(biphenyl-4-yl)butanoate (38 mg).

Workup

  1. stirringAfter stirring for 2.5 hours
  2. extractionthe products are extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe obtained residue is purified by silica gel flash column chromatography (heptane/EtOAc=100:0 to 0:100)

Sources & evidence

ORD record
ord-d6b0d04892bb4100ad0bc12c309f774a
Source dataset
uspto-grants-2014_09
Patent number
US08822534B2

Reaction notes

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