2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile → (1R,5S)-2,2,2-trichloroethyl-5-[[[(t-butyloxy)carbonyl]amino]oxy]-2-cyclopentene-1-carbamate

HRID 127791Notes

Reaction equation

HRID 127791 reaction equation
[Cl:1][C:2]([Cl:16])([Cl:15])[CH2:3][O:4][C:5](=[O:14])[NH:6][C@H:7]1[C@@H:11]([O:12][NH2:13])[CH2:10][CH:9]=[CH:8]1.[C:17]([O:21][C:22](ON=C(C1C=CC=CC=1)C#N)=[O:23])([CH3:20])([CH3:19])[CH3:18]>O1CCCC1>[Cl:1][C:2]([Cl:15])([Cl:16])[CH2:3][O:4][C:5](=[O:14])[NH:6][C@H:7]1[C@@H:11]([O:12][NH:13][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:23])[CH2:10][CH:9]=[CH:8]1

Participants

4

Reactant 2

HCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 12943968(1R,5S)-2,2,2-trichloroethyl-5-(aminooxy)-2-cyclopentene-1-carbamate

Product 1

HCID 12943984(1R,5S)-2,2,2-trichloroethyl-5-[[[(t-butyloxy)carbonyl]amino]oxy]-2-cyclopentene-1-carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An 7.8 g. quantity of crude (1R,5S)-2,2,2-trichloroethyl-5-(aminooxy)-2-cyclopentene-1-carbamate is dissolved in 25 ml. of tetrahydrofuran and 6.15 g (25 mm) of 2-(tertbutoxycarbonyloxyimino)-2-phenylacetonitrile and the mixture stirred for 22 hours at room temperature, 20 hours at 50° C., 72 hours at room temperature and then evaporated in vacuo. The residue is chromatographed over 900 g. of silica gel eluted with (15-85) ethylacetate-toluene. Three hundred ml. fractions are collected. The product is found in fractions 10-12. Evaporation and recrystallization of the residue from Skellysolve B yields (1R,5S)-2,2,2-trichloroethyl-5-[[[(t-butyloxy)carbonyl]amino]oxy]-2-cyclopentene-1-carbamate m.p. 83°-84° C. as a white solid.

Workup

  1. customevaporated in vacuo
  2. customThe residue is chromatographed over 900 g
  3. washof silica gel eluted with (15-85) ethylacetate-toluene
  4. customfractions are collected
  5. customEvaporation and recrystallization of the residue from Skellysolve B

Sources & evidence

ORD record
ord-75ee6477c97849189c49e6414904e58d
Source dataset
uspto-grants-1981_03
Patent number
US04256898

Reaction notes

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