HCID 88802391, compound → HCID 70616346, compound

HRID 2420566Notes

Reaction equation

HRID 2420566 reaction equation
C([NH:3][C@@H:4]1[C:21](=[O:22])[N:6]2[C:7]([C:13]([O:15][CH2:16][C:17]([Cl:20])([Cl:19])[Cl:18])=[O:14])=[C:8]([CH:11]=[CH2:12])[CH2:9][S:10][C@H:5]12)=O>CO>[ClH:18].[NH2:3][C@@H:4]1[C:21](=[O:22])[N:6]2[C:7]([C:13]([O:15][CH2:16][C:17]([Cl:19])([Cl:18])[Cl:20])=[O:14])=[C:8]([CH:11]=[CH2:12])[CH2:9][S:10][C@H:5]12

Participants

3

Reactant 1

HCID 88802391HCID 88802391, compound

Product 1

HCID 70616346HCID 70616346, compoundYield 168.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,2,2-Trichloroethyl 7β-formamido-3-vinylceph-3-em-4-carboxylate (0.88 g., 2.3 mmole) was treated with dry methanol (5 ml.), when some solid crystallised. The suspension was cooled to ca. 5° and stirred while phosphorus oxychloride (0.53 ml.) was added dropwise. The reaction mixture was kept at ca. 5° for 30 minutes and diluted with ether (20 ml.); no solid separated. The solvents were evaporated and the residual oil was treated with ether (ca. 10 ml.) to give a white solid. The solid was filtered off, washed with ether, and dried to give the title hydrochloride (0.765 g., 85%), λmax. (MeOH) 295 nm (ε 10,150), νmax. (Nujol), ca. 2590 (N+H3), 1788 (azetidin-2-one), 1730 (CO2R), and 946 cm-1 (=CH2), τ (Me2SO-d6), 2.86 (1H, dd, J 11 and 17.5 Hz; CH=CH2), 4.13 (1 H, d, J 17.5 Hz) and 4.45 (1H, d, J 11 Hz) (CH=CH2), 4.64 (1H, d, J 5 Hz; C7 -H), 4.78 (1H, d, J 5 Hz; C6 -H), 4.81 and 4.98 (2H, AB-q, J 12 Hz; CH2CCl3), 5.92 and 6.24 (2H, AB-q, J 17 Hz; C2 -H2), 6.31 (ca 1H, d, JP-H 11 Hz; ca. 0.1 M trimethyl phosphate) (Found: P, 0.78%).

Workup

  1. customcrystallised
  2. temperatureThe suspension was cooled to ca. 5°
  3. additionwas added dropwise
  4. additiondiluted with ether (20 ml.)
  5. customno solid separated
  6. customThe solvents were evaporated
  7. additionthe residual oil was treated with ether (ca. 10 ml.)
  8. customto give a white solid
  9. filtrationThe solid was filtered off
  10. washwashed with ether
  11. customdried

Sources & evidence

ORD record
ord-13bfd648da504680940f55a88cd78b0d
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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