tert-Butyl bromoacetate → HCID 131713915, compound

HRID 1632751Notes

Reaction equation

HRID 1632751 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O-:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Na+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 131712445Sodium 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 131713915HCID 131713915, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of sodium 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 5.0 g) in N,N-dimethylformamide (100 ml) was added tert-butyl bromoacetate (2.9 g), and the solution was stirred for 3 hours at ambient temperature. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and water in turn, and dried over anhydrous magnesium sulfate. The solution was evaporated in vacuo to give tert-butoxycarbonylmethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 3.2 g), mp 188°-190° C. (dec.).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate and water in turn
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solution was evaporated in vacuo

Sources & evidence

ORD record
ord-c14e526f6d2f4432b99b62c9234676a3
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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