Benzyl ((2R,3S)-2-(3,3-dibromoallyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate → Benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-(prop-2-yn-1-yl)azetidin-3-yl)(4-methoxybenzyl)carbamate

HRID 708472Notes

Reaction equation

HRID 708472 reaction equation
C([Li])(C)(C)C.Br[C:7](Br)=[CH:8][CH2:9][C@@H:10]1[C@H:13]([N:14]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12](=[O:34])[N:11]1[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=1[O:44][CH3:45]>C1COCC1>[CH3:45][O:44][C:37]1[CH:38]=[C:39]([O:42][CH3:43])[CH:40]=[CH:41][C:36]=1[CH2:35][N:11]1[C@H:10]([CH2:9][C:8]#[CH:7])[C@H:13]([N:14]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[C:15](=[O:24])[O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]1=[O:34]

Participants

4

Reactant 2

HCID 118379781Benzyl ((2R,3S)-2-(3,3-dibromoallyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamateHCID 178418306HCID 178418306, compound

Product 1

HCID 118379454Benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-(prop-2-yn-1-yl)azetidin-3-yl)(4-methoxybenzyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyllithium (0.291 mL, 0.494 mmol) was added to the solution of benzyl ((2R,3S)-2-(3,3-dibromoallyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)(4-methoxybenzyl)carbamate (162 mg, 0.235 mmol) in THF (Volume: 3.4 mL) at −78° C. After 15 min, the reaction mixture was quenched with NH4Cl, and diluted with water and EtOAc. The layers were separated, and the organic layer was extracted with EtOAc (2×). Combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified via silica gel chromatography (EtOAc-Hept, 0-40%) to afford the title compound (98 mg, 79%). LCMS: Rt=1.08 min, m/z=529.3 (M+1) Method 2m_acidic.

Workup

  1. customthe reaction mixture was quenched with NH4Cl
  2. additiondiluted with water and EtOAc
  3. customThe layers were separated
  4. extractionthe organic layer was extracted with EtOAc (2×)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified via silica gel chromatography (EtOAc-Hept, 0-40%)

Sources & evidence

ORD record
ord-fab519e07bbb45e39c897cd0be8fbf32
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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