HCID 86713346, compound → HCID 86713345, compound

HRID 928025Notes

Reaction equation

HRID 928025 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:10]1[CH2:13][N:12](C(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C.C(O)(=O)C>[C:31]([O:30][C:28]([NH:27][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:10]1[CH2:11][NH:12][CH2:13]1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

5

Reactant 1

HCID 86713346HCID 86713346, compound2×

Product 1

HCID 86713345HCID 86713345, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 3-[bis-(tert-butoxycarbonylamino)methyl]-1-(diphenylmethyl)azetidine (Intermediate 152, 6.4 g) and 10% palladium on carbon (3 g) in ethanol (100 mL) and acetic acid (2 mL) was stirred under an atmosphere of hydrogen overnight. The solid was filtered off and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and washed with saturated aqueous sodium carbonate, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM (10%) to give 3-[bis-(tert-butoxycarbonylamino)methyl]azetidine (4.0 g) as a colourless liquid, which was used without further characterisation.

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated aqueous sodium carbonate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of methanol and DCM (10%)

Sources & evidence

ORD record
ord-11492a5257e54646bf67cffe02f0259f
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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