Benzoyl chloride → HCID 66601302, compound

HRID 409885Notes

Reaction equation

HRID 409885 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[C:20]([NH:12][CH:10]1[CH2:11][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylate

Product 1

HCID 66601302HCID 66601302, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-Boc-3-aminoazetidine 1a (1.2 g, 6.98 mmol) and Et3N (2.4 mL, 17.3 mmol) in CH2Cl2 (70 mL) at 0° C. was added benzoyl chloride 1b (0.89 mL, 7.68 mmol). The reaction was kept at 0° C. for 3 h, quenched with aq. NaHCO3, and the resulting mixture was extracted with CH2Cl2. The organic solution was dried over Na2SO4 and concentrated. Purification by flash column chromatography (silica gel, 40% EtOAc/heptane) gave compound 1c (1.9 g).

Workup

  1. customquenched with aq. NaHCO3
  2. extractionthe resulting mixture was extracted with CH2Cl2
  3. dry with materialThe organic solution was dried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (silica gel, 40% EtOAc/heptane)

Sources & evidence

ORD record
ord-536a936dba024c3ea51e58cd1bef98f8
Source dataset
uspto-grants-2014_06
Patent number
US08759533B2

Reaction notes

Loading…