Methanol → HCID 67923927, compound

HRID 973864Notes

Reaction equation

HRID 973864 reaction equation
C1(CC([NH:10][C@@H:11]2[C:45](=[O:46])[N:13]3[C:14]([C:29]([O:31][CH:32]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])=[C:15](/[CH:18]=[C:19]4/[O:20][C:21]([C:23]5[C:28]/4=[CH:27][CH:26]=[CH:25][CH:24]=5)=[O:22])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>ClCCl.O>[NH2:10][C@@H:11]1[C:45](=[O:46])[N:13]2[C:14]([C:29]([O:31][CH:32]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])=[C:15](/[CH:18]=[C:19]3/[O:20][C:21]([C:23]4[C:28]/3=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:22])[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 67923937HCID 67923937, compound

Product 1

HCID 67923927HCID 67923927, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 7β-phenylacetamido-3-(E-phthalidylidenemethyl)ceph-3-em-4-carboxylate (1.3 g), dissolved in dichloromethane (10 mls) was cooled to -20° C. under argon. N-methylmorpholine (0.5ml) followed by a solution of phosphorous pentachloride (0.561 g) in dichloromethane (15 mls) were then added. After ca 30 mins, i.r. analysis showed no starting material. Dry methanol (10 mls) was added in one portion very rapidly, and the solution allowed to warm to room temperature over 30 mins. Water (20 mls) was added and the mixture vigorously stirred for 20-30 mins. After washing and drying the organic phase, the crude product was purified by flash chromatography, eluting with 70 and 80% ethyl acetate/hexane. The title compound was obtained as a pale yellow solid, (0.563 g, 53%), νmax (CH2Cl2) 1780(s), 1720, 1600(w,br), 1560 and 1210cm-1 ; δH (CDCl3) 3.56 (2H,ABq,J18.7Hz), 4.93 (1H,d,J5.1Hz), 5.10 (1H,d,J5.1Hz), 6.39(1H,s), 6.88 (1H,s), 7.21 (10H,m), 7.46-7.68 (3H,m), and 7.87 (1H,d,J7.6Hz); [mass spectrum: +ve ion (3-NOBA, Na+) M Na+, 532].

Workup

  1. additionwere then added
  2. waitAfter ca 30 mins
  3. temperatureto warm to room temperature over 30 mins
  4. washAfter washing
  5. customdrying the organic phase
  6. customthe crude product was purified by flash chromatography
  7. washeluting with 70 and 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6387d6aa900045eeae4a19fad7fedb49
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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