Acetic Acid → HCID 86739190, compound

HRID 2295968Notes

Reaction equation

HRID 2295968 reaction equation
C[O-].[Na+].[C:4]([O:8][C:9]([CH2:11][C:12](=[O:24])[C:13](=[N+:22]=[N-:23])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl[C@@H:26]1[N:29](C(=O)C(OCOC(=O)C(C)(C)C)=O)[C:28](=[O:43])[C@H:27]1[C:44]([OH:47])([CH3:46])[CH3:45].C(O)(=O)C>ClCCl>[C:4]([O:8][C:9]([CH:11]([C@H:26]1[NH:29][C:28](=[O:43])[C@@H:27]1[C:44]([OH:47])([CH3:46])[CH3:45])[C:12](=[O:24])[C:13](=[N+:22]=[N-:23])[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 53929570HCID 53929570, compoundHCID 86739189HCID 86739189, compound

Product 1

HCID 86739190HCID 86739190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To 50 ml of 0.2 M methanolic sodium methoxide solution stirred and cooled at -78° C., are successively added 3.43 g of 2,2,2-trichloroethyl 4-t-butyloxycarbonyl-2-diazo-3-oxobutyrate in 30 ml of dichloromethane and 10 mMol equivalent of pivaloyloxymethyl [3R,4S]-2-[4-chloro-3-(1-hydroxyisopropyl)-2-oxoazetidin-1-yl]-2-oxoacetate, which is prepared according to the procedure of Example 1, in 30 ml of dichloromethane. After a few minutes, 0.6 ml of acetic acid is added to the solution and the solution is evaporated to dryness under reduced pressure. The residue is taken into 50 ml of ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure to give the crude product. The product is subjected to silica-gel column chromatography by use of n-hexane-ethyl acetate=1:2 for elution. The fractions containing the desired compound are combined and concentrated to give 2.6 g of the titled compound.

Workup

  1. customis prepared
  2. waitAfter a few minutes
  3. customthe solution is evaporated to dryness under reduced pressure
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customto give the crude product
  8. washThe product is subjected to silica-gel column chromatography by use of n-hexane-ethyl acetate=1:2 for elution
  9. additionThe fractions containing the desired compound
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-31e2832988ba4e4186f93ffddafaf8fe
Source dataset
uspto-grants-1984_01
Patent number
US04427586

Reaction notes

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