Formaldehyde → HCID 13035130, compound

HRID 2419874Notes

Reaction equation

HRID 2419874 reaction equation
[I-].[C:2]1([CH:8]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[O:9][C:10]([C:12]2[N:17]3[C:18](=[O:29])[C@@H:19]([NH:20][C:21](=[O:28])[CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)[C@H:16]3[S:15][CH2:14][C:13]=2[CH:30]=[C:31]2C=CC=CC2[PH+](C2C=CC=CC=2)C2C=CC=CC=2)=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].C=O>C(Cl)Cl>[S:24]1[CH:25]=[CH:26][CH:27]=[C:23]1[CH2:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:29])[N:17]2[C:12]([C:10]([O:9][CH:8]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:11])=[C:13]([CH:30]=[CH2:31])[CH2:14][S:15][C@H:16]12)=[O:28]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium Bicarbonate2×HCID 131711204HCID 131711204, compound

Product 1

HCID 13035130HCID 13035130, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [4-diphenylmethoxycarbonyl-7β-(2-thienylacetamido)ceph-3-em-3-ylmethyly] triphenylphosphonium iodide (430 mg.), RF 0.0, in methylene chloride (10 ml.) was shaken with 5%-sodium bicarbonate solution (10 ml.) for five minutes. The separated organic layer was treated with 40%-formaldehyde solution (2 ml.) and 5% aqueous sodium bicarbonate solution (5 ml.) and the mixture stirred vigorously at room temperature until the chromophore of the starting material at 388 nm. had disappeared (ca. 30 minutes). The organic layer was separated and washed with 0.5N-hydrochloric acid and water, then dried and evaporated in vacuo. The residue was crystallised from methanol to give diphenylmethyl 7β-(2-thienylacetamido)-3-vinylceph-3-em-4-carboxylate (90 mg. 36%), RF 0.5, as needles, λmax. 296 nm. (ε 13,200), identified by infrared spectroscopy with material described previously.

Workup

  1. custom(ca. 30 minutes)
  2. customThe organic layer was separated
  3. washwashed with 0.5N-hydrochloric acid and water
  4. customdried
  5. customevaporated in vacuo
  6. customThe residue was crystallised from methanol

Sources & evidence

ORD record
ord-987a134464ce4ae6b072499dc55f2857
Source dataset
uspto-grants-1978_08
Patent number
US04107431

Reaction notes

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