1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[1-Phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl ester

HRID 606761Notes

Reaction equation

HRID 606761 reaction equation
[C:1]([N:18]1[CH2:21][CH:20]([C:22](O)=[O:23])[CH2:19]1)([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[C:46]([O:50][C:51]([N:53]1[CH2:58][CH2:57][C:56](=[C:59]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[C:60]([NH:62][NH2:63])=[O:61])[CH2:55][CH2:54]1)=[O:52])([CH3:49])([CH3:48])[CH3:47]>C(Cl)Cl.O>[C:46]([O:50][C:51]([N:53]1[CH2:54][CH2:55][C:56](=[C:59]([C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[C:60]([NH:62][NH:63][C:22]([CH:20]2[CH2:21][N:18]([C:1]([O:3][CH2:4][CH:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[C:12]4[C:17]3=[CH:16][CH:15]=[CH:14][CH:13]=4)=[O:2])[CH2:19]2)=[O:23])=[O:61])[CH2:57][CH2:58]1)=[O:52])([CH3:49])([CH3:47])[CH3:48]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 27561481-Fmoc-azetidine-3-carboxylic acidHCID 116169104-(1-Phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 670464624-[1-Phenyl-1-(2-(N-(9-fluorenylmethoxycarbonyl)-3-azetidinecarbonyl)-hydrazinocarbonyl)-methylene]-piperidine-1-carboxylic acid tert-butyl esterYield 101.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Fmoc-azetidine-3-carboxylic acid (0.495 g, 1.53 mmol) in CH2Cl2 (10 mL) was added HOBt (0.290 g, 2.14 mmol) and EDCI (0.411 g, 2.14 mmol), and the mixture was allowed to stir for 10 min. To this solution was added 4-(1-phenyl-1-hydrazinocarbonyl-methylene)piperidine-1-carboxylic acid tert-butyl ester (0.507 g, 1.53 mmol), the mixture was stirred for 1 h and then it was diluted with H2O and the layers separated. The aqueous phase was extracted with CH2Cl2 (×3) and the combined organic layers were washed (H2O, brine), dried (Na2SO4) and evaporated to give the title compound (0.99 g, 100%) which was of sufficient purity to be used as such in the following step:

Workup

  1. stirringthe mixture was stirred for 1 h
  2. customthe layers separated
  3. extractionThe aqueous phase was extracted with CH2Cl2 (×3)
  4. washthe combined organic layers were washed (H2O, brine)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-18b2ad7bae74419e82b95d5d0c06aaee
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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