Formaldehyde → HCID 70615839, compound

HRID 2420563Notes

Reaction equation

HRID 2420563 reaction equation
C=O.[C:3](=O)([O-])O.[Na+].[Br-].[C:9]1([CH2:15][C:16]([NH:18][C@@H:19]2[C:54](=[O:55])[N:21]3[C:22]([C:46]([O:48][CH2:49][C:50]([Cl:53])([Cl:52])[Cl:51])=[O:47])=[C:23]([CH2:26][P+](C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:24][S:25][C@H:20]23)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[C:9]1([CH2:15][C:16]([NH:18][C@@H:19]2[C:54](=[O:55])[N:21]3[C:22]([C:46]([O:48][CH2:49][C:50]([Cl:51])([Cl:53])[Cl:52])=[O:47])=[C:23]([CH:26]=[CH2:3])[CH2:24][S:25][C@H:20]23)=[O:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 88802404HCID 88802404, compound

Product 1

HCID 70615839HCID 70615839, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40%-Formaldehyde solution (3 ml.) and 4%-sodium hydrogen carbonate solution (6 ml.) were added to a solution of [7β-Phenylacetamido-4-(2,2,2-trichloroethoxycarbonyl)ceph-3-em-3-ylmethyl]-triphenylphosphonium bromide (403 mg., 0.5 mmole) in methylene chloride (10 ml.), and the two phase mixture was stirred vigorously for 25 minutes. The organic phase was washed with 2N-hydrochloric acid and water (10 ml of each), dried (MgSO4), and evaporated to an orange oil which was crystallised from ethanol (ca. 2 ml.) to give the title ester (22 mg., 9%), λmax. (EtOH) 297 nm (ε 14,100).

Workup

  1. washThe organic phase was washed with 2N-hydrochloric acid and water (10 ml of each),
  2. dry with materialdried (MgSO4)
  3. customevaporated to an orange oil which
  4. customwas crystallised from ethanol (ca. 2 ml.)

Sources & evidence

ORD record
ord-2d41f02e621a48bfa43352fed4ba7770
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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