Tetrahydrofuran → HCID 67774375, compound

HRID 1963080Notes

Reaction equation

HRID 1963080 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][N:9]2[C:12]([CH:30]=[O:31])=[C:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=3[CH3:29])[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:8]2[C:7]=1[Cl:32])=[O:5])[CH3:2].C=C(C)C.C1C[O:40]CC1.P([O-])(O)(O)=O.[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.[Cl-].[Na+].O.C(Cl)Cl.CC(=O)OCC>[Cl:32][C:7]1[C:8]2[N:9]([C:12]([C:30]([OH:40])=[O:31])=[C:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=3[CH3:29])[C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=[CH:11][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

Participants

11

Reactant 5

HCID 8028TetrahydrofuranHCID 8255IsobutyleneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 88415083HCID 88415083, compound

Product 1

HCID 67774375HCID 67774375, compoundYield 98.1%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound of step 7 (5.15 g, 11.42 mmol) was suspended in tert-butanol (90 ml), and a 2 M solution of isobutene in THF (34.27 ml, 68.53 mmol), a solution of sodium dihydrogenphosphate (4.111 g, 34.27 mmol) in 25 ml of water and sodium chlorite (1.937 g, 17.13 mmol) were added. The mixture was stirred at room temperature for 2 h. Then brine (200 ml), water (50 ml), EA (400 ml) and DCM (100 ml) were added and the organic phase was separated, dried over magnesium sulfate, filtered and evaporated to dryness. The obtained solid was triturated several times with cyclohexane and dried in vacuo at 50° C. 5.23 g of the title compound were obtained as a yellow solid melting at 193-194° C.

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe obtained solid was triturated several times with cyclohexane
  6. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-cb9884dede1c403091f0651d580a27b1
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

Loading…