Triphenylphosphine → HCID 54171448, compound

HRID 321939Notes

Reaction equation

HRID 321939 reaction equation
[Si:1]([N:8]1[C@@H:11]([CH2:12]O)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[SH:46][C:47]1[N:52]=[CH:51][CH:50]=[CH:49][N:48]=1>C1COCC1>[Si:1]([N:8]1[C@@H:11]([CH2:12][S:46][C:47]2[N:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11074788HCID 11074788, compoundHCID 178418793HCID 178418793, compound

Product 1

HCID 54171448HCID 54171448, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(tert-butyldimethylsilyl)-4(R)-(hydroxymethyl)azetidin-2-one (2.75 g, 12.77 mmol) in THF (80 mL) was added PPh3 (6.70 g, 25.54 mmol). The reaction was cooled at 0° and DEAD (3.3 mL, 25.54 mmol) was added dropwise. After 5 min. 2-mercaptopyrimidine (3.60 g, 31.92 mmol) was added. After stirring for 15 min at 0° and 60 h at room temperature, the reaction mixture was concentrated. The residue was treated with EtOAc/hexane (1/1) and the resulting solid was filtered and rinsed with Et2O. The filtrate was concentrated and purified by flash chromatography (SiO2, 25% EtOAc/hexane) to provide 1-(tert-butyldimethylsilyl)-4(R)-(pyrimidin-2-ylsulfanylmethyl)azetidin-2-one (3.75 g, 95% yield) as clear oil. 1H NMR (400 MHz, CDCl3) δ 8.70 (d, J=4.8 Hz, 2H), 7.20 (t, J=4.9 Hz, 1H), 4.08-4.01 (m, 2H), 3.41-3.36 (m, 1H), 3.99 (dd, J=14.3, 10.8 Hz, 1H), 2.98 (dd, J=15.6, 2.5 Hz, 1H), 1.18 (s, 9H), 0.53 (s, 3H), 0.49 (s, 3H).

Workup

  1. temperatureThe reaction was cooled at 0°
  2. concentrationthe reaction mixture was concentrated
  3. additionThe residue was treated with EtOAc/hexane (1/1)
  4. filtrationthe resulting solid was filtered
  5. washrinsed with Et2O
  6. concentrationThe filtrate was concentrated
  7. custompurified by flash chromatography (SiO2, 25% EtOAc/hexane)

Sources & evidence

ORD record
ord-74aee978ed1d4ee4900e499990511bb2
Source dataset
uspto-grants-2001_04
Patent number
US06211170B1

Reaction notes

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