N-(tert-Butoxycarbonyl)-1,5-diaminopentane → HCID 68525725, compound

HRID 1989831Notes

Reaction equation

HRID 1989831 reaction equation
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]([O:10][CH:11]1CCN(CCC(O)=O)CC1)=[O:9].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O:56][C:57]([NH:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][NH2:65])=O)(C)(C)C.[CH3:66][CH2:67][N:68]([CH:72]([CH3:74])C)[CH:69]([CH3:71])C>C(Cl)Cl>[NH2:65][CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][NH:59][C:57]([CH2:74][CH2:72][N:68]1[CH2:67][CH2:66][CH:11]([O:10][C:8](=[O:9])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:71][CH2:69]1)=[O:56]

Participants

6

Reactant 4

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 218806073-[4-(Biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic Acid

Product 1

HCID 68525725HCID 68525725, compoundYield 118.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[4-(biphenyl-2-ylcarbamoyloxy)piperidin-1-yl]propionic acid (3 g, 8.15 mmol; prepared as described in Preparation 3), HATU (4.65 g, 12.2 mmol), N-tert-butoxycarbonyl-1,5-diaminopentane (2.47 g, 12.2 mmol) and DIPEA (4.25 mL, 24.52 mmol) in 100 mL of DCM was stirred at room temperature for 1 hour. The reaction mixture was washed with a 1:1 solution of brine and 1N HCl (100 mL), water (100 mL), dried over magnesium sulfate, filtered and concentrated. The residue was treated with 20% TFA in DCM (100 mL) at room temperature for 2 hours. The solvent and TFA were removed under reduced pressure. The residue was taken up in 100 mL of DCM and washed with 1N NaOH (100 mL) and brine (100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to give 4.36 g of the title compound as a solid.

Workup

  1. washThe reaction mixture was washed with a 1:1 solution of brine and 1N HCl (100 mL), water (100 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue was treated with 20% TFA in DCM (100 mL) at room temperature for 2 hours
  6. customThe solvent and TFA were removed under reduced pressure
  7. washwashed with 1N NaOH (100 mL) and brine (100 mL)
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-608ff1611bfe496d82e13f4717cdecd8
Source dataset
uspto-grants-2010_01
Patent number
US07642355B2

Reaction notes

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