Methanol → HCID 131717078, compound

HRID 973880Notes

Reaction equation

HRID 973880 reaction equation
C1(CC([NH:10][C@@H:11]2[C:41](=[O:42])[N:13]3[C:14]([C:25]([O:27][CH:28]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:26])=[C:15](/[CH:18]=[C:19]4/[C:20](=[O:24])[O:21][CH2:22][CH2:23]/4)[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.CN1CCOCC1.P(Cl)(Cl)Cl.CO>ClCCl.O>[NH2:10][C@@H:11]1[C:41](=[O:42])[N:13]2[C:14]([C:25]([O:27][CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:26])=[C:15](/[CH:18]=[C:19]3/[C:20](=[O:24])[O:21][CH2:22][CH2:23]/3)[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24387Phosphorus trichlorideHCID 131717079HCID 131717079, compound

Product 1

HCID 131717078HCID 131717078, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Diphenylmethyl 7β-phenylacetamido-3-[E-2-oxotetrahydrofuran-3-ylidenemethyl)ceph-3-em-4-carboxylate, (0.38 g) in dry dichloromethane (3 mls), cooled to -20° C. under argon, was treated with N-methylmorpholine (0.146 g, 0.158 mls) and a solution of phosphorous trichloride (0.178 g) in dichloromethane (4.4 mls). After 30 mins at -20° C., methanol (5 mls) was added rapidly in one portion. The reaction mixture was allowed to warm slowly to room temperature over 30 mins, and then water (10 mls) added. After vigorous stirring for a further 30 mins the solvents were completely removed in vacuo. The residue was partitioned between ethyl acetate/hexane after adjusting the pH to 8 using aqueous 0.880 ammonia. After washing and drying the organic layer, the solvent was removed and the crude product triturated with ether. Flash chromatography on fine silica gel eluting with ethyl acetate afforded the title compound as a pale yellow foam, (0.116 g, 39%), νmax (CH 2 Cl2) 1780, 1750 and 1720cm-1 ; δH (CDCl3) 2.57-2.72 (1H, m), 2.80-2.96 (1H, m), 3.61 (2H, s), 4.07-4.26 (2H, m), 4.85 (1H, d, J 5.1Hz), 4.98 (1.1Hz), 4.98 (1H, d, J 5.1Hz), 7.04 (1Hz), 7.04 (1H, s) and 7.2-7.5 (10H, m); [mass spectrum: +ve ion (3NOBA, Na+) MNa+ 485].

Workup

  1. customwere completely removed in vacuo
  2. customThe residue was partitioned between ethyl acetate/hexane
  3. washAfter washing
  4. customdrying the organic layer
  5. customthe solvent was removed
  6. customthe crude product triturated with ether

Sources & evidence

ORD record
ord-2ee1a6388a10466e8a071e608e4e028d
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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