Trifluoroacetic acid → (3S-trans)-3-Benzyloxycarbonylamino-4-methylazetidinone

HRID 867645Notes

Reaction equation

HRID 867645 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[NH:11][C:10]1=[O:14])=[O:7])([CH3:4])(C)C.FC(F)(F)C(O)=O.[C:22]1(OC)[CH:27]=[CH:26]C=[CH:24][CH:23]=1>ClCCl>[CH2:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:12]([CH3:13])[NH:11][C:10]1=[O:14])=[O:7])[C:4]1[CH:26]=[CH:27][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 13155285tert-Butyl ((2S,3S)-2-methyl-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 13182463(3S-trans)-3-Benzyloxycarbonylamino-4-methylazetidinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.3 g of (3S-trans)-3-t-butoxycarbonylamino-4-methylazetidinone in 10 ml each of dichloromethane and anisole is cooled to 0° C. and 112 ml of trifluoroacetic acid is added. The solution is stirred for 90 minutes and evaporated in vacuo (benzene added and evaporated three times). The residue is dissolved in 70 ml of acetone and the solution is adjusted to pH 7 with 5% sodium bicarbonate solution. A total of 5.33 g of benzyl chloroformate is added over 1 hour at pH 6.5-7.5. The mixture is stirred for 30 minutes at pH 7, diluted with 100 ml of saturated salt, and extracted with ethyl acetate (three 400 ml portions). The residue obtained by evaporation is chromatographed on a 1 liter silica gel column. Elution with chloroform-ethyl acetate (4:1) gives 2.19 g of compound. Crystallization from ether-hexane yields 1.125 g of the title compound.

Workup

  1. customevaporated in vacuo (benzene added and evaporated three times)
  2. dissolutionThe residue is dissolved in 70 ml of acetone
  3. additionA total of 5.33 g of benzyl chloroformate is added over 1 hour at pH 6.5-7.5
  4. stirringThe mixture is stirred for 30 minutes at pH 7
  5. additiondiluted with 100 ml of saturated salt
  6. extractionextracted with ethyl acetate (three 400 ml portions)
  7. customThe residue obtained by evaporation
  8. customis chromatographed on a 1 liter silica gel column
  9. washElution with chloroform-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-3836e6be5b8f4c979ba2efd305ad8ee8
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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