Tetrahydrofuran → HCID 22399015, compound

HRID 1770011Notes

Reaction equation

HRID 1770011 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:10]([C:12]([O:14]C(OCC)C)=[O:13])[OH:11])=O)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].CS(Cl)(=O)=O.[CH2:37]1[CH2:41][O:40][CH2:39][CH2:38]1>CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]1[O:14][C:12](=[O:13])[CH:10]([O:11][CH:39]([O:40][CH2:41][CH3:37])[CH3:38])[CH:9]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:8]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 67615395HCID 67615395, compound

Product 1

HCID 22399015HCID 22399015, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 409 mg (1.16 mmol) of N-tertbutoxycarbonyl-O-(1-ethoxyethyl)-3-phenylisoserine (3) in 20 mL of THF is added 261 mg (2.33 mmol) of solid potassium tert-butoxide and the mixture is stirred at 25° C. for 30 min. A solution of 134 mg (1.16 mmol) of methanesulfonyl chloride in 3.2 mL of THF is added and the mixture is stirred at 25° C. for 1.5 hour. The mixture is diluted with 80 mL of hexane an ethyl acetate and this solution is extracted with 20 mL of saturated aqueous sodium bicarbonate solution and 10 mL of brine. The organic phase is dried over sodium sulfate and concentrated to give 235 mg (70%) of 2-tertbutoxy-4-phenyl-5-(1-ethoxyethoxy)-4,5-dihydro-1,3-oxazin-6-one as a colorless oil.

Workup

  1. stirringthe mixture is stirred at 25° C. for 1.5 hour
  2. extractionthis solution is extracted with 20 mL of saturated aqueous sodium bicarbonate solution and 10 mL of brine
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3f30d81b8294b1eab5260d78f8954e8
Source dataset
uspto-grants-1995_01
Patent number
US05384399

Reaction notes

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