HCID 13583686, compound → HCID 70300000, compound

HRID 2287524Notes

Reaction equation

HRID 2287524 reaction equation
[Si:1]([N:8]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][C:9]1=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[CH2:20][C:21]([CH2:23][O:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[CH2:22]>C1COCC1>[Si:1]([N:8]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:10]([CH2:22][C:21]([CH2:23][O:24][C:25](=[O:34])[C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)=[CH2:20])[C:9]1=[O:18])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 13583686HCID 13583686, compoundHCID 18704701HCID 18704701, compound

Product 1

HCID 70300000HCID 70300000, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of N2, a 1.5M solution of LiN(Pri)2THF in c-C6H6 (Aldrich; 43.9 ml, 65.9 mmol) was added dropwise to a stirred solution of 1-tert-butyldimethylsilyl-4-phenyl-2-azetidinone (13.24 g, 50.64 mmol) in dry THF (230 ml) at an inner temperature between -78 and -73 C. After stirring at -78 C for 30 minutes, the reaction mixture became a white slurry. A solution of 3-bromo-2-[(4-methoxybenzoyloxy)methyl]propene (14.69 g, 54.18 mmol) in dry THF (30.0 ml) was added dropwise at an inner temperature between -78 and -71 C. After the addition was complete, the dropping funnel used was rinsed with dry THF (5 ml×2). The resultant homogeneous reaction mixture was stirred at -78 C. for an hour, and then at -10 C. for 50 minutes. The reaction was quenched by adding sat. NH4Cl aq. solution (30.0 ml) below 0 C. The mixture was taken up in AcOEt (500 ml). The AcOEt solution separated was washed with sat. NaCl aq. solution (100 ml×2), dried (MgSO4), and concentrated in vacuo to give a heterogeneous yellow oil (26.51 g). This was, then, diluted with Et2O (250 ml), washed with H2O (×2), and sat. NaCl aq. solution (×1), dried (MgSO4), and concentrated in vacuo to give a homogeneous yellow oil (24.91 g). This was flash chromatographed over SiO2 (Merck Kieselgel 60, 250 g). Elution with n-hexane-AcOEt (40:1/30:1/20:1/10:1) gave title compound (19.73 g, 86.3%) as a viscous pale yellow oil. IRmax (film): 1745(s), 1645(m), 1610(m), 1510(m), 990(shoulder, m), 910(m), 775(m), 745(w), 700(m), 680(m) cm-1 ; 1H-NMR δ: 7.40-7.25(m, 5H), 7.20(d, J=8.8 Hz, 2H), 6.85(d, J=8.8 Hz, 2H), 5.05(s, 1H), 4.84(s, 1H), 4.35(s, 2H), 4.20(d, J=2.6 Hz, 1H), 3.86(s, 2H), 3.80(s, 3H), 3.25(ddd, J=10.5, 5.1, 2.6 Hz, 1H), 2.70(dd, J=15.7, 5.1 Hz, lH), 2.48(dd, J=15.7, 10.7 Hz, 1H), 0.92(s, 9H), 0.21(s, 3H), -0.21(s, 3H) ppm.

Workup

  1. additionAfter the addition
  2. washthe dropping funnel used was rinsed with dry THF (5 ml×2)
  3. stirringThe resultant homogeneous reaction mixture was stirred at -78 C
  4. waitfor an hour
  5. waitfor 50 minutes
  6. customThe reaction was quenched
  7. additionby adding sat. NH4Cl aq. solution (30.0 ml) below 0 C
  8. customThe AcOEt solution separated
  9. washwas washed with sat. NaCl aq. solution (100 ml×2)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26a1ef7479ef473c9e878f5c6d46cf30
Source dataset
uspto-grants-2000_07
Patent number
US06083943

Reaction notes

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