Benzoyl chloride → HCID 69949926, compound

HRID 353274Notes

Reaction equation

HRID 353274 reaction equation
[CH:1]([C@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[O:9][Si:10]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:11][CH3:12])([CH3:3])[CH3:2].[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:17]([N:7]1[C@H:4]([CH:1]([CH3:2])[CH3:3])[C@H:5]([O:9][Si:10]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:11][CH3:12])[C:6]1=[O:8])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 69894359HCID 69894359, compound

Product 1

HCID 69949926HCID 69949926, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (+)-cis-4-isopropyl-3-triethylsilyloxy-azetidin-2-one (486 mg, 2.00 mmole), benzoyl chloride (0.255 mL, 1.1 equiv), diisopropylethyl amine (0.346 mL, 1.2 equiv) and p-dimethylaminopyridine (244 mg, 1 equiv) in dry DCM (6 mL) was left stirring at 0° C. for 6 hr. The bath was removed and the reaction was left stirring overnight. It was then diluted with DCM and washed with water, aq. HCl solution (0.1 N), saturated aq. NaHCO3 solution, brine and dried (Na2SO4). Removal of the solvent followed by silica gel column chromatography (gradient elution with 0 to 5% EtOAc in hexane) gave the title compound: 1H NMR δ (CDCl3) 0.47-0.94 (m, 21H), 2.09 (m, 1H), 4.07 (m, 1H), 4.75 (m, 1H), 7.24-7.76 (m, 5H).

Workup

  1. customThe bath was removed
  2. waitthe reaction was left
  3. stirringstirring overnight
  4. additionIt was then diluted with DCM
  5. washwashed with water, aq. HCl solution (0.1 N), saturated aq. NaHCO3 solution, brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent
  8. washfollowed by silica gel column chromatography (gradient elution with 0 to 5% EtOAc in hexane)

Sources & evidence

ORD record
ord-8fd3157067c544feb592a27cd1268bf9
Source dataset
uspto-grants-2004_06
Patent number
US06750246B1

Reaction notes

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