Triethylamine → HCID 15117237, compound

HRID 1029628Notes

Reaction equation

HRID 1029628 reaction equation
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.C(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[C:39]([C:42]1[CH2:43][CH2:44][N:45]([C:48]([O:50][CH2:51][C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[O:49])[CH2:46][CH:47]=1)(=[O:41])[CH3:40]>ClCCl.O.C(OCC)(=O)C>[CH2:51]([O:50][C:48]([N:45]1[CH2:44][CH:43]=[C:42]([C:39](=[O:41])[CH2:40][C@H:5]2[NH:8][C:7](=[O:9])[C@@H:6]2[C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH3:11])[CH2:47][CH2:46]1)=[O:49])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 65367Trimethylsilyl triflate2×HCID 10935078AzetidonHCID 15117236HCID 15117236, compound

Product 1

HCID 15117237HCID 15117237, compoundYield 75.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (3.96 g) and triethylamine (2.03 ml) in dichloromethane (60 ml) was added dropwise trimethylsilyl trifluoromethanesulfonate (3.5 ml) at -70° C. under nitrogen atmosphere. To this solution was added dropwise at -70° C. a reaction mixture, which had been prepared by stirring a solution of 4-acetyl-1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine (3.268 g), triethylamine (1.94 ml) and trimethylsilyl trifluoromethanesulfonate (2.6 ml) in dichloromethane at -70° C. under nitrogen atmosphere. After the mixture was warmed to ambient temperature, the mixture was stirred for 2 hours. The reaction mixture was poured into a mixture of ethyl acetate (200 ml) and water (100 ml), and the solution was stirred for 30 minutes. The organic layer was separated, washed with brine (100 ml), dried over magnesium sulfate and concentrated to give an oil, which was chromatographed on silica gel (300 ml) eluting with a mixture of hexane and ethyl acetate (2:1-1:5, V/V) to give (3S,4R)-4-[2-(1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (4.65 g).

Workup

  1. additionTo this solution was added dropwise at -70° C. a reaction mixture, which
  2. customhad been prepared
  3. stirringthe solution was stirred for 30 minutes
  4. customThe organic layer was separated
  5. washwashed with brine (100 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give an oil, which
  9. customwas chromatographed on silica gel (300 ml)
  10. washeluting with a mixture of hexane and ethyl acetate (2:1-1:5, V/V)

Sources & evidence

ORD record
ord-b2120d0ba6c04642a203893690d95f8b
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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