HCID 53656896, compound → HCID 57076211, compound

HRID 861890Notes

Reaction equation

HRID 861890 reaction equation
[CH:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[C:5](=[O:15])[C@H:4]1[NH:16][C:17](=[O:25])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.[O:26]1[CH2:30][CH2:29][CH2:28][C@H:27]1[C:31]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:32]>C(#N)C>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C@H:3]([CH:1]=[CH:33][C:31](=[O:32])[C@@H:27]3[CH2:28][CH2:29][CH2:30][O:26]3)[C@H:4]([NH:16][C:17](=[O:25])[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]2=[O:15])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 53656896HCID 53656896, compoundHCID 57147329HCID 57147329, compound

Product 1

HCID 57076211HCID 57076211, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of (3S,4S)-4-formyl-1-(4-methoxyphenyl)-3-phenylacetamidoazetidin-2-one (10.39 g, 30.7 mmol) in acetonitrile (250 ml) was treated with (S)-tetrahydrofuran-2-ylcarbonylmethylenetriphenylphosphorane (11.50 g, 30.7mmol) and stirred at room temperature for 2 days. The bulk of the product was collected by filtration and washed with acetonitrile. The remainder of the product was purified by chromatography on silica gel eluting with ethyl acetate yielding a further 1.66 g. The title compound was isolated as a white solid (total 12.12 g, 91%); m.p. 159°-162° C.; [α]D -83.4° (c=1 CHCl3); (Found: C, 69.41; H, 6.28; N, 6.20%; M+, 434.1832. C25H26N2O5 requires: C, 69.11; H, 6.03; N, 6.45%; M 434.11842); ννmax (CHCl3) 3414, 1751, 1682, 1631, 1513 and 1250 cm-1 ; δH (CDCl3) 1.75-1.92 (3H, m), 2.18 (1H, m), 3.57 (2H, s), 3.76 (3H, s), 3.70-3.90 (2H, m), 4.39 (1H, m), 4.88 (1H, t, J 5.4 Hz), 5.49 (1H, dd, J 8.0, 5.4 Hz), 6.20 (1H, d, J 8.0 Hz), 6.60 (1H, d, J 16.1 Hz), 6.78-6.85 (3H, m) and 7.18-7.38 (7H, m).

Workup

  1. filtrationThe bulk of the product was collected by filtration
  2. washwashed with acetonitrile
  3. customThe remainder of the product was purified by chromatography on silica gel eluting with ethyl acetate yielding a further 1.66 g

Sources & evidence

ORD record
ord-4c5b15d87dfb41b290b501800f8b9f5c
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

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