Sodium Cyanide → HCID 54342562, compound

HRID 399518Notes

Reaction equation

HRID 399518 reaction equation
[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2].[C-:25]#[N:26].[Na+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:24])[C@@H:7]1[CH2:11][C@@H:10]([C:25]#[N:26])[CH2:9][N:8]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 10861453HCID 10861453, compound

Product 1

HCID 54342562HCID 54342562, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (4R)-1-(tert-butyloxycarbonyl)-4-(methane-sulfonyloxy)-L-proline tert-butyl ester (889 mg, 2.43 mmol) and sodium cyanide (1.19 g, 24.3 mmol) in N,N-dimethylformamide (18 mL) was stirred for 4 days at 80° C. under a nitrogen atmosphere. The cooled reaction mixture was diluted with ethyl acetate (100 mL), washed with water (2×), saturated brine solution, dried (Na2SO4), and evaporated. The crude product mixture was subjected to flash silica gel chromatography eluting initially with 10% ethyl acetate/hexane. Fractions containing the TLC more mobile isomer were combined and evaporated to afford the desired title compound; yield 225 mg (31%).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (2×), saturated brine solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. washeluting initially with 10% ethyl acetate/hexane
  6. additionFractions containing the TLC more mobile isomer
  7. customevaporated

Sources & evidence

ORD record
ord-0062e6c0ed8b4351bd8c1523156689ff
Source dataset
uspto-grants-1998_10
Patent number
US05821261

Reaction notes

Loading…