Potassium Phosphate, Dibasic → Benzyl ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

HRID 708315Notes

Reaction equation

HRID 708315 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C@H:9]([CH2:10][N:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])[C@H:8]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:7]1=[O:28].OP([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[O:28]=[C:7]1[C@@H:8]([NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:9]([CH2:10][N:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])[NH:6]1

Participants

4

Reactant 2

HCID 24450Potassium Phosphate, Dibasic3×HCID 118411331Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

Product 1

HCID 118411330Benzyl ((3S,4R)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamateYield 62%

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 benzyl ((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate (3.84 g, 8.18 mmol), K2S2O8 (3.10 g, 11.5 mmol) and K2HPO4 (1.852 g, 10.6 mmol) in ACN:water (2:1, 136 mL) while heating for 40 min at 90° C. More K2S2O8 (663 g, 2.45 mmol) and K2HPO4 (370 mg, 2.13 mmol) were added and it was heated for another 3 h. More K2S2O8 (332 mg, 1.23 mmol) and K2HPO4 (185 mg, 1.06 mmol) were added, and it was heated for an additional 2 h, whereupon it was concentrated in vacuo, removing most of the ACN. The mixture was diluted with brine/EtOAc and the layers were separated. The aqueous layer was extracted with EtOAc (3×) and the combined organic layers were dried over Na2SO4. The crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-100% then MeOH-DCM, 10%) to afford the title compound (1.61 g, 62%) as a beige foam. LCMS: Rt=0.51 min, m/z=320.0 (M+1) Method 2m_acidic.

Workup

  1. temperatureit was heated for another 3 h
  2. temperatureit was heated for an additional 2 h, whereupon it
  3. concentrationwas concentrated in vacuo
  4. customremoving most of the ACN
  5. additionThe mixture was diluted with brine/EtOAc
  6. customthe layers were separated
  7. extractionThe aqueous layer was extracted with EtOAc (3×)
  8. dry with materialthe combined organic layers were dried over Na2SO4
  9. customThe crude residue was purified via silica gel chromatography (EtOAc-Heptane, 0-100%

Sources & evidence

ORD record
ord-15be6179fcdb4fb48c6c90a456407735
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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