Phosphorus oxychloride → HCID 70595001, compound

HRID 2398134Notes

Reaction equation

HRID 2398134 reaction equation
P(Cl)(Cl)([Cl:3])=O.C([NH:8][C@@H:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13]([CH2:16][S:17][C:18]3[S:19][C:20]([CH3:23])=[N:21][N:22]=3)[CH2:14][S:15][C@H:10]12)=O>CO>[ClH:3].[NH2:8][C@@H:9]1[C:40](=[O:41])[N:11]2[C:12]([C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])=[C:13]([CH2:16][S:17][C:18]3[S:19][C:20]([CH3:23])=[N:21][N:22]=3)[CH2:14][S:15][C@H:10]12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 88784431HCID 88784431, compound

Product 1

HCID 70595001HCID 70595001, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Phosphorus oxychloride (1.8 ml) was added dropwise during 2 minutes to a stirred and cooled (0°) suspension of diphenylmethyl 7β-formamido-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylceph-3-em-4-carboxylate (4.1g) in dry methanol. After 30 minutes the yellow solution was concentrated under reduced pressure. Ethyl acetate was added to the residue and the resulting solid was collected and washed with ether to give the title hydrochloride λmax. (EtOH) 266 nm (ε 11,300),νmax. (Nujol) include 2590 (NH3+), 1778 (β-lactam) and 1710cm.-1 (ester), τ values (DMSO-d6) include 0.50 (broad m; NH3), 2.3-2.7 (m; phenyl protons), 3.02 (s; CHPh2), 4.66 + 4.76 (m; C-7 H and C-6 H), 5.39 + 5.69 (2ds, branches of quartet, J 13 Hz; C-3 CH2S). 6.15 (singlet; C-2CH2) and 7.36 (singlet; CH3).

Workup

  1. temperaturecooled
  2. concentrationAfter 30 minutes the yellow solution was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. customthe resulting solid was collected
  5. washwashed with ether

Sources & evidence

ORD record
ord-923e580191074954a1ab6fde63e91860
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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