Hydrochloric Acid → HCID 20081437, compound

HRID 1609445Notes

Reaction equation

HRID 1609445 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[N:12]=[C:11]([NH:17][S:18]([CH:21]([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])(=[O:20])=[O:19])[N:10]=1.IC.Cl>O1CCCC1.CCOCC.O>[CH3:7][O:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[N:12]=[C:11]([NH:17][S:18]([C:21]([CH3:1])([CH:26]([CH3:28])[CH3:27])[C:22]([O:24][CH3:25])=[O:23])(=[O:20])=[O:19])[N:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 20081442HCID 20081442, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20081437HCID 20081437, compoundYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

Potassium t-butoxide (5.3 g) was added with stirring and cooling to the product of Example 1 (7.5 g) in dry tetrahydrofuran (120 ml). The mixture was stirred for 41/2 hours at room temperature, and was then cooled to 5° C., when iodomethane (3.2 g) in dry tetrahydrofuran (10 ml) was added dropwise. Stirring was continued at room temperature for 24 hours, and the intermittently for 7 days. The solvent was run off under vacuum, and the residue was stirred with ice, water and ether while being acidified to pH=1 with hydrochloric acid. The ether solution was separated, the aqueous layer being extracted twice more with ether, and the combined ether extracts were washed with water (twice), dried over magnesium sulfate, and run down under vacuum to give the desired product (7.1 g) in am impure form. Purification by flash chromatography on silica gel, eluting with dichloromethane and ethyl acetate (9:1), followed by preparative HPLC gave 0.4 g of the pure desired product, mp 124°-127° C.

Workup

  1. stirringThe mixture was stirred for 41/2 hours at room temperature
  2. stirringStirring
  3. waitthe intermittently for 7 days
  4. customThe ether solution was separated
  5. extractionthe aqueous layer being extracted twice more with ether
  6. washthe combined ether extracts were washed with water (twice),
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-261d27a6b75f4ef7b4e96c3f44918cd5
Source dataset
uspto-grants-1995_03
Patent number
US05401710

Reaction notes

Loading…