Trimethylsilyl triflate → HCID 15117214, compound

HRID 1029612Notes

Reaction equation

HRID 1029612 reaction equation
[C:1]([C:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][CH2:13][CH:14]=[CH2:15])=[O:11])[CH2:8][CH:9]=1)(=[O:3])[CH3:2].FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C(O[C@H:32]1[NH:35][C:34](=[O:36])[C@@H:33]1[C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH3:38])(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C.[Br-].[Zn+2].[Br-].O.C(N(CC)CC)C>[CH2:13]([O:12][C:10]([N:7]1[CH2:6][CH:5]=[C:4]([C:1](=[O:3])[CH2:2][C@H:32]2[NH:35][C:34](=[O:36])[C@@H:33]2[C@H:37]([O:39][Si:40]([C:43]([CH3:44])([CH3:46])[CH3:45])([CH3:42])[CH3:41])[CH3:38])[CH2:9][CH2:8]1)=[O:11])[CH:14]=[CH2:15]

Participants

10

Reactant 4

HCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 10935078AzetidonHCID 15117213HCID 15117213, compound

Product 1

HCID 15117214HCID 15117214, compoundYield 65.1%

Reagents, catalysts & solvents 5

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4-acetyl-1-allyloxycarbonyl-1,2,3,6-tetrahydropyridine (1.33 g) and triethylamine (1.06 ml) in dichloromethane (50 ml) was added trimethylsilyl trifluoromethanesulfonate (2.2 ml) at 0° C. After stirring for 4 hours, a solution of (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (1.82 g) and zinc bromide (1.86 g) in ethyl acetate (10 ml) was added to the mixture, and the resultant mixture was stirred for 1 hour at 0° C. The reaction mixture was taken up into a mixture of ethyl acetate (200 ml) and water (200 ml). After adjusting pH to 4 with aqueous sodium hydrogen carbonate, the organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (40 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V) to give (3S,4R)-4-[2-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (1.80 g).

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent
  5. customgave a residue, which
  6. customwas chromatographed on silica gel (40 g)
  7. washeluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V)

Sources & evidence

ORD record
ord-ac1a1423fbac4c7faef18b975b639c49
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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