Potassium Phosphate, Dibasic → HCID 118379844, compound

HRID 708460Notes

Reaction equation

HRID 708460 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[N:14](CC2C=CC(OC)=CC=2OC)[C@@H:13]1[CH2:28][N:29]1[C:33](=[O:34])[CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:30]1=[O:42])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C:15](=[O:16])[NH:14][C@@H:13]1[CH2:28][N:29]1[C:33](=[O:34])[CH2:32][N:31]([C:35]([O:37][C:38]([CH3:40])([CH3:39])[CH3:41])=[O:36])[C:30]1=[O:42])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24450Potassium Phosphate, DibasicHCID 118379896HCID 118379896, compound

Product 1

HCID 118379844HCID 118379844, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

Prepared in an analogous manner to example 4, step 2 using tert-butyl 3-(((2R,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl)-2,4-dioxoimidazolidine-1-carboxylate (900 mg, 1.70 mmol) K2S2O8 (280 mg, 2.89 mmol), and K2HPO4 (680 mg, 2.91 mmol) in ACN:water (2:1, 30 mL) while heating at 90° C. for 4 h. After cooling to rt, the mixture was filtered and the filtrate was concentrated in vacuo, removing most of the ACN. The mixture was diluted with water/EtOAc and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 2-6%) to afford the title compound (170 mg, 23%). LCMS: m/z=431.0 (M−1).

Workup

  1. temperatureAfter cooling to rt
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customremoving most of the ACN
  5. additionThe mixture was diluted with water/EtOAc
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with EtOAc
  8. dry with materialthe combined organic layers were dried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 2-6%)

Sources & evidence

ORD record
ord-bd7162ac574d42a5a5a5df64444ccd19
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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