Phosphorus oxychloride → HCID 70595001, compound

HRID 1707183Notes

Reaction equation

HRID 1707183 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 (4.1 g) 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 (ε11,300), νmax. (Nujol) include 2590 (NH3+), 1778 (β-lactam) and 1710 cm.-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-2 CH2 ) 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-847ebe8cd14748988b9f7272438219b1
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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