Diethyl Ether → HCID 88784456, compound

HRID 2398150Notes

Reaction equation

HRID 2398150 reaction equation
[C:1]([S:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30]C=O)[C:28](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].P(Cl)(Cl)([Cl:36])=O.CCOCC>CO.CCOCC>[ClH:36].[C:1]([S:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH2:30])[C:28](=[O:33])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24813Phosphorus oxychlorideHCID 88783904HCID 88783904, compound

Product 1

HCID 88784456HCID 88784456, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

Procedure

A stirred suspension of diphenylmethyl 3-acetylthiomethyl-7β-formamidoceph-3-em-4-carboxylate (0.505 g) in methanol: ether (1:1, 3 ml) at 0° was treated over 10 min. with phosphorous oxychloride (0.468 g). The ice bath was removed and stirring continued for a further 20 min, when a clear solution resulted. The reaction was cooled to 0°, and a white crystalline precipitate appeared. Ether (15 ml) was added and the precipitate filtered off, washed with ether and dried in vacuo to give diphenylmethyl 3-acetylthiomethyl-7β-aminoceph-3-em-4-carboxylate hydrochloride (0.456 g, 89%) as white microcrystals; m.p. 155 -160° (d) [α]D - 91° (c 0.83 in DMSO), λmax (EtOH) 268 nm (ε 8,700)νmax. (Nujol) 1770 (β-lactam), 1720 (CO2R), 1702 cm.-1 (SCOCH3), τ (DMSO-d6) values include 2.60 (m; Ph), 3.02 (s, CHPh2), 7.66 (s, SCOCH3).

Workup

  1. customThe ice bath was removed
  2. customwhen a clear solution resulted
  3. temperatureThe reaction was cooled to 0°
  4. filtrationthe precipitate filtered off
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-1d4743bd81e54a98a9c282490172f06b
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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