tert-Butanol → HCID 131715743, compound

HRID 2231322Notes

Reaction equation

HRID 2231322 reaction equation
[N:1]([C:4]1[CH2:5][C@@H:6]2[CH2:20][C:19](=[O:21])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[N+]=[N-].C(O)(C)(C)C.[H][H]>O1CCOCC1.[Pd]>[NH2:1][C:4]1[CH2:5][C@@H:6]2[CH2:20][C:19](=[O:21])[N:7]2[C:8]=1[C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 131715738HCID 131715738, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131715743HCID 131715743, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

An ambient temperature mixture of benzyl 2-azido-carbapen-2-em-3-carboxylate (7.7 mg, 27 micromol) and palladium on calcium carbonate poisoned with lead (12.8 mg) in dry dioxane (0.80 ml) containing t-butanol (50 microliter) was stirred while hydrogen was bubbled through for 20 min. The mixture was filtered and the solid washed with diethyl ether (3×0.5 ml). The combined filtrate and washes were concentrated to 0.5 ml under vacuum, and the residue was chromatographed on one 20 cm×20 cm 250 micron silica gel preparative thin layer chromatography plate developed with 1:1 (v/v) toluene-ethyl acetate. The band centered at Rf 0.2 was eluted with ethyl acetate and the eluate was evaporated under vacuum to provide 2.6 mg (37%) benzyl 2-amino-carbapen-2-em-3-carboxylate as a light yellow glass; I.R. (neat film): 3450, 3330, 1780, 1690 cm-1 ; NMR (CDCl3): δ2.81 dd (J1 =4 Hz, J2 =16 Hz, 1H), 2.93 m (2H), 3.21 dd (J1 =5 Hz, J2 =16 Hz, 1H), 5.25 d (J=13 Hz, 1H), 5.32 d (J=13 Hz, 1H), 7.37 m (5H).

Workup

  1. customwas bubbled through for 20 min
  2. filtrationThe mixture was filtered
  3. washthe solid washed with diethyl ether (3×0.5 ml)
  4. concentrationThe combined filtrate and washes were concentrated to 0.5 ml under vacuum
  5. customthe residue was chromatographed on one 20 cm×20 cm 250 micron silica gel preparative thin layer chromatography plate
  6. washwas eluted with ethyl acetate
  7. customthe eluate was evaporated under vacuum

Sources & evidence

ORD record
ord-4d3ee52662ca4d42870ddee0f892aa0e
Source dataset
uspto-grants-1988_11
Patent number
US04782051

Reaction notes

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