Water → HCID 70523889, compound

HRID 1902512Notes

Reaction equation

HRID 1902512 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[C:19]1([CH2:25][C:26]([NH:28][CH:29]2[C:41](=[O:42])[N:31]3[CH:32]([C:38]([OH:40])=[O:39])[CH:33]([CH2:36][OH:37])[CH2:34][S:35][C@H:30]23)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CS(C)=O.C(OCC)(=O)C>[C:19]1([CH2:25][C:26]([NH:28][CH:29]2[C:41](=[O:42])[N:31]3[CH:32]([C:38]([O:40][CH2:8][C:7]4[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)=[O:39])[CH:33]([CH2:36][OH:37])[CH2:34][S:35][C@H:30]23)=[O:27])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 70523673HCID 70523673, compound

Product 1

HCID 70523889HCID 70523889, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Nitrobenzyl bromide (1.64 g.) and triethylamine (0.73 g.) were added to a solution of 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylic acid (2.0 g.) in dimethylsulfoxide (20 ml.) and stirred at room temperature for an hour. The resultant solution was poured into a solution of water (200 ml.) and ethyl acetate (200 ml.), and the organic layer was separated. Water (200 ml.) was added to the organic layer and then adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate and concentrated under reduced pressure. The residue was pulverized with diisopropyl ether to give 4-nitrobenzyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (2.1 g.).

Workup

  1. customthe organic layer was separated
  2. additionWater (200 ml.) was added to the organic layer
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride in turn, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7db24481ac6948e286b68c889c6e94bd
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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