2-Methylbenzenesulfonic acid → HCID 18704226, compound

HRID 2288290Notes

Reaction equation

HRID 2288290 reaction equation
[OH:1][CH2:2][C:3]1([CH2:22][OH:23])[C:7](=[O:8])[N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[C:5](=[O:21])[NH:4]1.[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.[C:30]1(C)[C:31](S(O)(=O)=O)=[CH:32][CH:33]=C[CH:35]=1.C(=O)(O)[O-:42].[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.O.O1CCCC1>[O:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]1[O:23][CH2:22][C:3]1([CH2:2][O:1][CH:33]2[CH2:32][CH2:31][CH2:30][CH2:35][O:42]2)[C:7](=[O:8])[N:6]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:18])([F:20])[F:19])[CH:10]=2)[C:5](=[O:21])[NH:4]1

Participants

9

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 15340927HCID 15340927, compound

Product 1

HCID 18704226HCID 18704226, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

331 mg of the product obtained in Stage 4 above, 4 ml of tetrahydrofuran, 1 ml of 3,4-dihydro-2H-pyran and 16 mg of p. toluene sulphonic acid, and H2O are introduced. After 35 minutes, the reaction medium is poured into 10 ml of sodium bicarbonate+1 ml of triethylamine and extraction is carried out with 3×10 ml of chloroform, the extracts are washed with a saturated aqueous solution of sodium chloride, dried and evaporated to dryness. After chromatography on silica, eluting with methylene chloride-acetone: 9-1, 500 mg of expected product (friable white foam) is obtained.

Workup

  1. washthe extracts are washed with a saturated aqueous solution of sodium chloride
  2. customdried
  3. customevaporated to dryness
  4. washAfter chromatography on silica, eluting with methylene chloride-acetone

Sources & evidence

ORD record
ord-3b0049f4c1554c8785928c53af77d66d
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

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