Triethylamine → HCID 68141868, compound

HRID 1729677Notes

Reaction equation

HRID 1729677 reaction equation
[Cl:1][C@@:2]1([CH3:25])[C@H:7]([C:8]([OH:10])=[O:9])[N:6]2[C:11](=[O:24])[C@@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:5]2[S:4][CH2:3]1.[N+:26]([C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1)([O-:28])=[O:27].C(N(CC)CC)C>CN(C)C=O>[Cl:1][C@@:2]1([CH3:25])[C@H:7]([C:8]([O:10][CH2:33][C:32]2[CH:35]=[CH:36][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=2)=[O:9])[N:6]2[C:11](=[O:24])[C@@H:12]([NH:13][C:14](=[O:23])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:5]2[S:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 68142344HCID 68142344, compound

Product 1

HCID 68141868HCID 68141868, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3β-chloro-3α-methyl-7β-phenoxyacetamidocepham-4α-carboxylic acid (2.74 g), p-nitrobenzyl bromide (1.52 g), and triethylamine (1 ml) in dimethylformamide (30 ml) is kept at room temperature for 3 hours. The reaction mixture is poured into ice water, and extracted with ethyl acetate. The extract solution is washed with water, dried, and evaporated in vacuo to give p-nitrobenzyl 3β-chloro-3α-methyl-7β-phenoxyacetamidocepham-4α-carboxylate (3.45 g). Yield: 93%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract solution is washed with water
  3. customdried
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-6dca412e7a0547a288b5f9363682e84a
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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