Tetrahydrofuran → HCID 21837264, compound

HRID 1739758Notes

Reaction equation

HRID 1739758 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]([Si:12]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[O:13][C:14]1[CH:32]=[CH:31][C:17]2[C:18](OS(C(F)(F)F)(=O)=O)=[CH:19][C:20](=[O:22])[O:21][C:16]=2[C:15]=1[CH3:33])([CH3:11])[CH3:10].C1COCC1.OP([O-])(O)=O.[Na+]>C(OCC)(=O)C>[CH3:10][C:9]([Si:12]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:13][C:14]1[CH:32]=[CH:31][C:17]2[C:18]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:19][C:20](=[O:22])[O:21][C:16]=2[C:15]=1[CH3:33])([CH3:8])[CH3:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 531671-MethylpiperazineHCID 21837274HCID 21837274, compoundHCID 23672064Monosodium phosphate

Product 1

HCID 21837264HCID 21837264, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.25 ml of N-methyl piperazine is added to a solution containing 2.53 g of 7-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-methyl-4-[[(trifluoromethyl)sulphony]oxy]-2H-1-benzopyran-2-one and 22 ml of THF. The reaction medium is maintained under agitation for 1 hour, poured into a 1M aqueous solution of sodium acid phosphate, and extraction is carried out with ethyl acetate. The organic phases are combined, washed, dried and concentrated under reduced pressure. Chromatography is carried out on silica eluting with a methanol-methylene chloride mixture (6-94). 2.31 g of sought product is isolated. rf=0.3.

Workup

  1. temperatureThe reaction medium is maintained under agitation for 1 hour
  2. washwashed
  3. customdried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fed90a61c7e148b5a59c7348cbc78b52
Source dataset
uspto-grants-1999_10
Patent number
US05968939

Reaction notes

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