Methanol → HCID 67923924, compound

HRID 973869Notes

Reaction equation

HRID 973869 reaction equation
[CH3:1][C:2]1=[C:3]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:4](=[O:43])[O:5]/[C:6]/1=[CH:7]/[C:8]1[CH2:9][S:10][C@@H:11]2[C@H:31]([NH:32]C(=O)CC3C=CC=CC=3)[C:30](=[O:42])[N:12]2[C:13]=1[C:14]([O:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].CO.O>ClCCl>[NH2:32][C@@H:31]1[C:30](=[O:42])[N:12]2[C:13]([C:14]([O:16][CH:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:15])=[C:8](/[CH:7]=[C:6]3\[C:2]([CH3:1])=[C:3]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[C:4](=[O:43])[O:5]\3)[CH2:9][S:10][C@H:11]12

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 67923950HCID 67923950, compound

Product 1

HCID 67923924HCID 67923924, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 3-(E-2,5-dihydro-4-methyl-2-oxo-3-phenylfuran-5-ylidenemethyl)-7β-phenylacetamidoceph-3-em-4-carboxylate (0.6 g) in dichloromethane (5 mls) under argon, was cooled to -20° C. N-methylmorpholine phosphorous pentachloride (0.253 g) in dichloromethane (6.075 mls). The solution was maintained at -20° C. for 30-40mins. I.r. analysis showed no starting material present Dry methanol (5 mls) was added rapidly, in one portion. The reaction mixture was allowed to warm to room temperature over 30mins. Water (10 mls) was then added and the solution vigorously stirred for 30 mins. The organic phase was separated, washed with brine and then dried. After removal of solvent the residue was purified by flash chromatography on silica gel, eluting with 70% ethyl acetate/hexane. The title compound was obtained as a yellow foam, (0.453 g, 92%), νmax (CH2Cl2) 1780 (shoulder), 1760, 1720(w) and 1615(vw)cm-1 ; δH (CDCl 3) 2.06 (3H,s), 3.47 (2H,ABq,J18.6Hz), 4.87 (1H,d,J5.1Hz), 5.00 (1H,d,J5.1Hz), 6.33 (1H,s), 7.00 (1H,s) and 7.1-7.5 (15H,m); [mass spectrum: +ve ion (3-NOBA, Na+) MNa+, 573].

Workup

  1. additionwas added rapidly, in one portion
  2. temperatureto warm to room temperature over 30mins
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customAfter removal of solvent the residue
  7. customwas purified by flash chromatography on silica gel
  8. washeluting with 70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-54d3a25d27e74374b2991759018664fa
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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