Pentane → HCID 15058003, compound

HRID 867665Notes

Reaction equation

HRID 867665 reaction equation
C[Si](C)(C)[C:3]#[C:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCCCC>ClCCl>[C:4]([C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[CH:3]

Participants

5

Reactant 3

HCID 8003PentaneHCID 2724141Tetrabutylammonium FluorideHCID 15058001HCID 15058001, compound

Product 1

HCID 15058003HCID 15058003, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-(trans)-4-[2-(trimethylsilyl)ethynyl]-2-oxo-3-[(triphenylmethyl)amino]azetidine (2.97 g) is dissolved in 30 ml of dichloromethane and 330 mg of tetrabutylammonium fluoride (containing 20-25% water) is added. After 20 minutes, the solvent is removed in vacuo. The residue is taken up in ethyl acetate and water. The organic layer is separated, washed once with water and once with saturated aqueous sodium chloride, dried over sodium sulfate, and filtered. Removal of the solvent gives an oil which is stirred for 15 minutes with 60 ml of pentane to afford 2.35 g of the title compound as a powder (after drying in vacuo).

Workup

  1. customthe solvent is removed in vacuo
  2. customThe organic layer is separated
  3. washwashed once with water and once with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customRemoval of the solvent
  7. customgives an oil which

Sources & evidence

ORD record
ord-384d9a05475e410a821f9254958bc508
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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