Hydroquinone → HCID 11256464, compound

HRID 1825349Notes

Reaction equation

HRID 1825349 reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([CH2:11][C@H:12]2[N:15]([C:16](=P(CCCC)(CCCC)CCCC)[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:14](=[O:36])[C@@H:13]2[C@H:37]([OH:39])[CH3:38])=O)=[N:4]1)[CH3:2].C1(C=CC(O)=CC=1)O.C(OCC)(=O)C.CCCCCC.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:39][C@@H:37]([C@H:13]1[C:14](=[O:36])[N:15]2[C:16]([C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])=[C:9]([C:5]3[CH:6]=[C:7]([CH3:8])[N:3]([CH2:1][CH3:2])[N:4]=3)[CH2:11][C@H:12]12)[CH3:38]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 8857Ethyl AcetateHCID 21226206Ethyl acetate hexaneHCID 86586090HCID 86586090, compound

Product 1

HCID 11256464HCID 11256464, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Allyl 2-{(3S,4R)-4-[(1-ethyl-5-methylpyrazol-3-yl)carbonylmethyl]-3-[(R)-1-hydroxyethyl]-2-oxoazetidinyl}-2-(tri-n-butylphosphoranylidene)acetate (2.6), in toluene (120 ml) containing hydroquinone (20 mg) was heated under reflux in an argon atmosphere for 4 h, allowed to stand for 64 h, and then heated under reflux for a further 2 h. The mixture was cooled and then loaded onto a column (4.5×12 cm) of silica gel (particle size 0.040-0.063 mm), elutin with ethyl acetate/hexane mixtures; 1:1; 6:4; 7:3; 8:2; 9:1 (250 ml of each), followed by ethyl acetate. This Dave the carbapenem (436 mg); υmax(CH2Cl2) 3604, 2976, 1774, 1716, 1600, 1546, 1311, 1189 cm−1; λmax(EtOH)/nm 321.5 (ε/dm3 mol−1 cm−1 14,856), δ(CDCl3) 1.36 (d, J 6.3 Hz), 1.39 (t, J7.3 Hz) (together 5H), 1.80 (1H, d, J 5.0 Hz), 2.28 (3H,s), 3.19 (1H, dd J 2.7 & 6.7 Hz), 3.28 (1H, dd, J 9.0 & 18.6 Hz), 3.60 (1H, dd, J 9.9 & 18.5 Hz), 4.08 (2H, q, J 7.3 Hz), 4.16-4.30 (2H, m), 4.68-4.90 (2H, m), 5.27 (1H, m, approx d, J ca. 12 Hz), 5.46 (m, approx d, J ca. 17 Hz), 5.93-6.08 (1H, m), 7.00 (1H, s) ppm; [Found m/z 345.1693. C18H23N3O4 requires m/z 345.1689].

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an argon atmosphere for 4 h
  3. temperatureheated
  4. temperatureunder reflux for a further 2 h
  5. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-b6d7b12e1f634864b5bba228873707ea
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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