Water → HCID 22144941, compound

HRID 1824950Notes

Reaction equation

HRID 1824950 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:23])[CH2:10][C:11]1[C:19]2[O:18][CH:17](Cl)[CH:16]([Cl:21])[C:15]=2[CH:14]=[C:13]([F:22])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1OCCOCCOCCOCCOCCOC1.O.[Cl-].[NH4+]>CC(C)([O-])C.[K+].C(O)(C)(C)C.C(OCC)C>[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:23])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[C:16]([Cl:21])[C:15]=2[CH:14]=[C:13]([F:22])[CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 22144937HCID 22144937, compound

Product 1

HCID 22144941HCID 22144941, compoundYield 56.2%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent2×HCID 23665647Potassium tert-butoxideSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 0.30 gm (0.82 mMol) N-tert-butoxycarbonyl 1-(2,3-dichloro-2,3-dihydro-5-fluorobenzofur-7-yl)-2-aminopropane and 0.135 gm 18-crown-6 in 6.5 mL 1M potassium tert-butoxide in tert-butanol was stirred at 35° C. for 1 hour. The reaction mixture was diluted with 4 mL tert-butanol was continued for an additional 2.5 hours. The reaction mixture was cooled to room temperature and diluted with 50 mL diethyl ether followed by 5 mL water and 20 mL saturated aqueous ammonium chloride. The phases were separated and the aqueous phase was extracted with 25 mL diethyl ether. The organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure to provide an off-white solid. This solid residue was subjected to silica gel chromatography, eluting with hexane containing 7% ethyl acetate. Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 0.151 gm (56%) of the desired compound as a white solid.

Workup

  1. waitwas continued for an additional 2.5 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with 25 mL diethyl ether
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide an off-white solid
  8. washeluting with hexane containing 7% ethyl acetate
  9. additionFractions containing the desired compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e85bd65773d74001a3c4f1d445ba7988
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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