Formaldehyde → HCID 88802464, compound

HRID 2420568Notes

Reaction equation

HRID 2420568 reaction equation
[CH2:1]=[O:2].[C:3](=O)([O-])O.[Na+].[Br-].[C:9]1([CH:15]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:16][C:17]([C:19]2[N:24]3[C:25](=[O:30])[C@@H:26]([NH:27]C=O)[C@H:23]3[S:22][CH2:21][C:20]=2[CH2:31][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH:1]([NH:27][C@@H:26]1[C:25](=[O:30])[N:24]2[C:19]([C:17]([O:16][CH:15]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:18])=[C:20]([CH:31]=[CH2:3])[CH2:21][S:22][C@H:23]12)=[O:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 18607841HCID 18607841, compound

Product 1

HCID 88802464HCID 88802464, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

40%-Aqueous formaldehyde solution (10 ml.) and 3%-sodium hydrogen carbonate solution (30 ml.) were added to a vigorously stirred solution of [4-diphenylmethoxycarbonyl-7β-formamidoceph-3-em-3-ylmethyl]-triphenylphosphonium bromide (1.875 g., 2.5 mmole) in methylene chloride (20 ml.). The two-phase mixture was stirred for 25 minutes and the organic phase was washed with 2N-hydrochloric acid and water (20 ml of each), dried (MgSO4), and evaporated to an orange foam (1.68 g.). This foam was chromatographed on Kieselgel G (Merck, 75 g.) with 10- and 17%-acetone in methylene chloride as eluants. The appropriate fractions were combined and evaporated to give the title ester as a pale-yellow crystalline solid (334 mg., 32%), m.p. 148° to 152° (decomp), [α]D23 - 66° (c 1.19; Me2SO), λmax. (EtOH) 295 nm (ε 9,350), νmax. (CHBr3), (NH), 1787 (azetidin-2-one), 1725 (CO2R), and 1696 and 1500 cm-1 (CONH), τ (CDCl3) 1.78 (1H, s; CHO), 2.4 to 2.8 (10 H, m; (C6H5)2CH), 2.96 (1H, dd, J 11 and 18 Hz; CH=CH2), 3.01 (1H, s; (C6H5)2CH), 3.29 (1H, d, J 9 Hz; NH), 4.12 (1H, dd, J 9 and 5 Hz; C7 -H), 4.55 (1H, d, J 18 Hz) and 4.72 (1H, d, J 11 Hz) (CH=CH2), 5.02 (1H, d, J 5 Hz; C6 -H), 6.34 and 6.57 (2H, AB-q, J 18 Hz; C2 -H2).

Workup

  1. washthe organic phase was washed with 2N-hydrochloric acid and water (20 ml of each),
  2. dry with materialdried (MgSO4)
  3. customevaporated to an orange foam (1.68 g.)
  4. customThis foam was chromatographed on Kieselgel G (Merck, 75 g.) with 10- and 17%-acetone in methylene chloride as eluants
  5. customevaporated

Sources & evidence

ORD record
ord-36ffac5288874ca590755c2c5c68610a
Source dataset
uspto-grants-1978_08
Patent number
US04110534

Reaction notes

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