Diisopropylethylamine → HCID 58243413, compound

HRID 2361684Notes

Reaction equation

HRID 2361684 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14]C3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.Cl.[NH:34]1[CH2:37][CH:36]([C:38]([O:40][CH3:41])=[O:39])[CH2:35]1>C(O)(C)C.CO>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:34]3[CH2:37][CH:36]([C:38]([O:40][CH3:41])=[O:39])[CH2:35]3)=[O:14])[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 21100040Methyl azetidine-3-carboxylate hydrochlorideHCID 58243404HCID 58243404, compound

Product 1

HCID 58243413HCID 58243413, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 4-nitrophenyl 4-cyclobutyl-1,4-diazepane-1-carboxylate (2.4 g, 7.5 mmol) in isopropyl alcohol (6 ml) and methanol (3 ml) was added DIPEA (3.80 ml, 24 mmol) followed by methyl azetidine-3-carboxylate hydrochloride (1.70 g, 11 mmol) portion wise over 2 minutes. The resulting suspension was heated at 85° C. for 72 h. The mixture was allowed to cool and the solvent was removed in vacuo. The residue was dissolved in DCM (100 ml) and washed with 1M sodium carbonate solution (3×30 ml), dried (Na2SO4), filtered and evaporated at reduced pressure. Purification by FCC on silica provided the title compound as pale yellow oil (0.95 g, 43%).

Workup

  1. temperatureto cool
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in DCM (100 ml)
  4. washwashed with 1M sodium carbonate solution (3×30 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated at reduced pressure
  8. customPurification by FCC on silica

Sources & evidence

ORD record
ord-a75368dcf339406b99ce6d0c6c6517a1
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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