6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid → HCID 86736285, compound

HRID 1390221Notes

Reaction equation

HRID 1390221 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].[C:16]([O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]O)=[CH:22][CH:21]=1)(=[O:18])[CH3:17].C1(N=C=NC2CCCCC2)CCCCC1>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][CH2:24][C:23]1[CH:22]=[CH:21][C:20]([O:19][C:16](=[O:18])[CH3:17])=[CH:27][CH:26]=1)=[O:11]

Participants

6

Reactant 4

HCID 1626-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 959064-Acetoxybenzyl alcoholHCID 5360545Sodium

Product 1

HCID 86736285HCID 86736285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, sodium salt (5 mmole) in 50 ml of dimethylformamide is stirred at room temperature while 2 equivalents of p-(acetyloxy)benzyl alcohol is added. The mixture is cooled to 0° C. after which 5.5 mmole of dicyclohexylcarbodiimide in 10 ml of dimethylformamide is added. This mixture is stirred at 0° C. for 1 hour and at room temperature for 4 hours. Dicyclohexylurea is removed by filtration. The filtrate is diluted with chloroform, washed with water, dried over magnesium sulfate, filtered and evaporated to give the title compound.

Workup

  1. additionis added
  2. additionis added
  3. customDicyclohexylurea is removed by filtration
  4. additionThe filtrate is diluted with chloroform
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-23945efe59484475a016cebaa630f743
Source dataset
uspto-grants-1979_02
Patent number
US04138397

Reaction notes

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