Sodium Chloride → HCID 57261052, compound

HRID 1090530Notes

Reaction equation

HRID 1090530 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[O:6])[CH:2]=[CH2:3].C(O[C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[C@H:28]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH3:29])(=O)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[Cl-].[Na+]>ClCCl.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[CH:13]=[C:14]([CH3:18])[C:15](=[O:17])[CH2:16][C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[C@H:28]([O:30][Si:31]([C:34]([CH3:35])([CH3:37])[CH3:36])([CH3:33])[CH3:32])[CH3:29])=[O:6])[CH:2]=[CH2:3]

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 65367Trimethylsilyl triflateHCID 10935078AzetidonHCID 57259370HCID 57259370, compound

Product 1

HCID 57261052HCID 57261052, compoundYield 71.5%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-allyloxycarbonyl-2-(2-methyl-3-oxo-1-butenyl)piperidine (9.9 g), (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (17.0 g) and triethylamine (16.5 ml) in dichloromethane (100 ml) was added trimethylsilyl trifluoromethanesulfonate (28.6 ml at -15° C. After stirring at 0° C. for 2 hours, the reaction mixture was taken up into a mixture of ethyl acetate (200 ml) and water (200 ml). The mixture was stirred for 2 hours at ambient temperature. After addition of sodium chloride (40 g), the organic layer was separated, washed with saturated sodium hydrogen carbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (300 ml) eluting with a mixture of n-hexane and ethyl acetate (5:1-7:3, V/V) to give (3S,4R)-4-[4-(1-allyloxycarbonylpiperidin-2-yl)-3-methyl-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (13.48 g).

Workup

  1. stirringThe mixture was stirred for 2 hours at ambient temperature
  2. customthe organic layer was separated
  3. washwashed with saturated sodium hydrogen carbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (300 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (5:1-7:3, V/V)

Sources & evidence

ORD record
ord-d684702391ae4c2097383fa78f7266c7
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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