Dimethyl Sulfoxide → (2R)-2-(BOC)amino-N-(3-oxo-azetidine-1-yl)-3-(4-chlorophenyl)propionamide

HRID 1670030Notes

Reaction equation

HRID 1670030 reaction equation
[C:1]([NH:8][C@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10]([NH:12][N:13]1[CH2:16][CH:15]([OH:17])[CH2:14]1)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(Cl)(=O)C(Cl)=O.CS(C)=O>C(Cl)Cl>[C:1]([NH:8][C@H:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([NH:12][N:13]1[CH2:14][C:15](=[O:17])[CH2:16]1)=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 67345448(2R)-2-(BOC)Amino-N-(3-hydroxyazetidine-1-yl)-3-(4-chlorophenyl)propionamide

Product 1

HCID 67345314(2R)-2-(BOC)amino-N-(3-oxo-azetidine-1-yl)-3-(4-chlorophenyl)propionamideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-(BOC)Amino-N-(3-hydroxyazetidine-1-yl)-3-(4-chlorophenyl)propionamide (3.54 g, 10 mmol) was placed in a round-bottomed flask, filled with nitrogen, and DCM (30 mL) and oxalyl chloride (872 μl, 10 mmol) were added. The mixture was cooled to −78-C, and DMSO (709 μl, 10 mmol) was added. The reaction solution was stirred for 3 h keeping the temperature below −50° C. The reaction mixture was quenched by addition of TEA and warmed to rt. The reaction solution was diluted with a saturated aqueous NH4Cl solution, and the organic material was extracted with EtOAc. The extracts was dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (eluent: EtOAc/Hex=1/3) to give the title compound (2.88 g, 84%).

Workup

  1. additionwere added
  2. additionwas added
  3. customthe temperature below −50° C
  4. customThe reaction mixture was quenched by addition of TEA
  5. additionThe reaction solution was diluted with a saturated aqueous NH4Cl solution
  6. extractionthe organic material was extracted with EtOAc
  7. dry with materialThe extracts was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by column chomatography (eluent: EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-ab4d5dbf84bd4802a95abf73df053b48
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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