6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → HCID 20441282, compound

HRID 1390220Notes

Reaction equation

HRID 1390220 reaction equation
[NH2:1][CH:2]1[C:8](=[O:9])[N:7]2[CH:3]1[S:4][C:5]([CH3:14])([CH3:13])[CH:6]2[C:10]([OH:12])=[O:11].[Na].[CH3:16][C:17]1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O.C(Br)C.Cl>C(OCC)(=O)C.O.CN(C)C=O>[NH2:1][CH:2]1[C:8](=[O:9])[N:7]2[CH:3]1[S:4][C:5]([CH3:14])([CH3:13])[CH:6]2[C:10]([O:12][CH2:16][CH3:17])=[O:11]

Participants

9

Reactant 5

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 110826-Aminopenicillanic acidHCID 5360545Sodium2×

Product 1

HCID 20441282HCID 20441282, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, sodium salt, hereinafter referred to as 6-APA, sodium salt, (5.0 mmole) is added to 50 ml of dimethylformamide at room temperature. After stirring for 15 minutes, 5.5 mmole of ethyl bromide is added. This mixture is stirred for 2 to 3 hours after which it is diluted with ethyl acetate and water. The pH is adjusted to about 6.5 to 7.0 by the addition of hydrochloric acid and the organic phase is separated from the aqueous phase. The organic phase is washed with water, dried over magnesium sulfate, filtered and evaporated to give the title compound.

Workup

  1. stirringThis mixture is stirred for 2 to 3 hours after which it
  2. customthe organic phase is separated from the aqueous phase
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-2f24aed8327d439b906e8e732fdb4e1a
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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