Formaldehyde → HCID 88802391, compound

HRID 2420565Notes

Reaction equation

HRID 2420565 reaction equation
[CH2:1]=[O:2].[C:3](=O)([O-])O.[Na+].[Br-].C([NH:11][C@@H:12]1[C:47](=[O:48])[N:14]2[C:15]([C:39]([O:41][CH2:42][C:43]([Cl:46])([Cl:45])[Cl:44])=[O:40])=[C:16]([CH2:19][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:17][S:18][C@H:13]12)=O>C(Cl)Cl>[CH:1]([NH:11][C@@H:12]1[C:47](=[O:48])[N:14]2[C:15]([C:39]([O:41][CH2:42][C:43]([Cl:44])([Cl:45])[Cl:46])=[O:40])=[C:16]([CH:19]=[CH2:3])[CH2:17][S:18][C@H:13]12)=[O:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 88802291HCID 88802291, compound

Product 1

HCID 88802391HCID 88802391, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40%-Aqueous formaldehyde solution (4 ml.) and 4%-aqueous sodium hydrogen carbonate solution (6 ml.) were added to a vigorously stirred solution of [7β-formamido-4-(2,2,2-trichloroethoxycarbonyl)ceph-3-em-3-ylmethyl]-triphenylphosphonium bromide (357 mg., 0.5 mmole) in methylene chloride (20 ml.). The two-phase mixture was stirred for 45 minutes, and the organic phase was washed with 2N-hydrochloric acid and water (20 ml. of each), dried (MgSO4), and evaporated to an oil (0.35 g). This was subjected to preparative-layer chromatography on Kieselgel G (Merck PF254+366) using 20% acetone in methylene chloride as eluant to give the title ester as a cream foam (84 mg., 43.5%), λmax. (EtOH) 297.5 nm (ε 10,700), τ (CDCl3) 1.69 (1H, s; CHO), 2.81 (1H, dd, J 11.5 and 18 Hz; CH=CH2), 3.24 (1H, d, J 9 Hz; NH), 4.05 (1H, dd, J 9 and 4.5 Hz; C7 -H), 4.43 (1H, d, J 18 Hz) and 4.55 (1H, d, J 11.5 Hz) (CH=CH2), 4.90 (1H, d, J 4.5 Hz; C6 -H), 4.94 and 5.20 (2H, AB-q, J 12 Hz; CH2CCl3), 6.22 and 6.45 (2H, AB-q, J 18 Hz; C2 -H2).

Workup

  1. washthe organic phase was washed with 2N-hydrochloric acid and water (20 ml
  2. dry with materialof each), dried (MgSO4)
  3. customevaporated to an oil (0.35 g)

Sources & evidence

ORD record
ord-4aa02579f2064f069b2a05b1f0726734
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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