Trifluoroacetic acid → HCID 70602156, compound

HRID 972278Notes

Reaction equation

HRID 972278 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH:7]([N:12]1[C:18](=[O:19])[CH:17]2[CH:13]1[S:14][C:15]([CH3:21])([CH3:20])[NH:16]2)[CH2:8][C:9]([OH:11])=[O:10])(C)(C)C.F[C:24](F)(F)C(O)=O>>[CH3:1][O:5][C:6](=[O:22])[CH:7]([N:12]1[C:18](=[O:19])[CH:17]2[CH:13]1[S:14][C:15]([CH3:21])([CH3:20])[NH:16]2)[CH2:8][C:9]([O:11][CH3:24])=[O:10]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70602375HCID 70602375, compound

Product 1

HCID 70602156HCID 70602156, compound

Procedure

A mixture of 0.025 g of the isomer B of α-(3,3-dimethyl-7-oxo-4-thia-2,6-diaza-6-bicyclo[3,2,0]heptyl)-α-(carboxymethyl)-acetic acid tert.-butyl ester (Example 39) and 1 ml of trifluoroacetic acid is kept for 18 hours at 0°, is then evaporated under reduced pressure, and the residue containing the α-(3,3-dimethyl-7-oxo-4-thia-2,6-diaza-6-bicyclo [3,2,0]heptyl)-α-(carboxymethyl-acetic acid, is taken up in 1 ml of dioxane and then mixed with an ether solution of diazomethane until saturated. After 3 minutes reaction time, the mixture is evaporated under reduced pressure and the residue is filtered through a silica gel column (diameter: 0.8 cm; hight: 10 cm), a 2:1-mixture of hexane and ethyl acetate being used for elution; the isomer B of α-(3,3-dimethyl-7-oxo-4-thia-2,6-diaza-6-bicyclo[3,2,0]heptyl)-α-(carbomethoxymethyl)-acetic acid methyl ester of the formula ##STR56## which is obtained as a crude product, melts at 136°-137° after recrystallisation from a mixture of ether, methylene chloride and hexane.

Workup

  1. customis then evaporated under reduced pressure
  2. additionthe residue containing the α-(3,3-dimethyl-7-oxo-4-thia-2,6-diaza-6-bicyclo [3,2,0]heptyl)-α-(carboxymethyl-acetic acid
  3. additionmixed with an ether solution of diazomethane until saturated
  4. customAfter 3 minutes reaction time
  5. customthe mixture is evaporated under reduced pressure
  6. filtrationthe residue is filtered through a silica gel column (diameter
  7. washhight: 10 cm), a 2:1-mixture of hexane and ethyl acetate being used for elution

Sources & evidence

ORD record
ord-eaabdd8b4a0540bdb52cde9512e60616
Source dataset
uspto-grants-1977_10
Patent number
US04052408

Reaction notes

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