Triisodecyl phosphite → t-Butyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate 1-oxide

HRID 2052097Notes

Reaction equation

HRID 2052097 reaction equation
[C:1]([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:14]([CH2:19][Br:20])[CH:15](Br)[S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(OCCCCCCCC(C)C)(OCCCCCCCC(C)C)OCCCCCCCC(C)C>C(OCC)C>[C:1]([NH:9][CH:10]1[C:28](=[O:29])[N:12]2[C:13]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[C:14]([CH2:19][Br:20])[CH2:15][S:16](=[O:17])[C@H:11]12)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 117488Triisodecyl phosphiteHCID 70462499t-Butyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate 1-oxide

Product 1

HCID 70462724t-Butyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate 1-oxideYield 44.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The remainder of the solution of the 2-bromo-3-bromomethyl compound obtained was used as such in the following debromination process. To this solution which contained at most 14.4 mmoles of t-butyl 7-benzamido-2-bromo-3-bromomethyl-3-cephem-4-carboxylate 1-oxide, were added 14 ml (approximately 25 mmoles) of triisodecyl phosphite and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was then washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness and upon addition of a small quantity of acetone, a brown precipitate was formed. Upon addition of diethyl ether, the brown precipitate was decolored almost completely and after standing for one night in the refrigerator, the precipitate was filtered off to obtain 3.0 g (44.6%) of t-butyl 7-benzamido-3-bromomethyl-3-cephem-4-carboxylate 1-oxide.

Workup

  1. washThe reaction mixture was then washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness and upon addition of a small quantity of acetone
  5. customa brown precipitate was formed
  6. waitafter standing for one night in the refrigerator
  7. filtrationthe precipitate was filtered off

Sources & evidence

ORD record
ord-76ae1f5151b74353803b8b6ab8a51290
Source dataset
uspto-grants-1980_01
Patent number
US04182870

Reaction notes

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