1-(3-Chloropropyl)-4-fluorobenzene → HCID 86760294, compound

HRID 719670Notes

Reaction equation

HRID 719670 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([SH:17])([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].Cl[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1>CC#N>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([S:17][CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)([CH3:16])[CH3:15])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 129320831-(3-Chloropropyl)-4-fluorobenzeneHCID 15225634HCID 15225634, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 86760294HCID 86760294, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a CH3CN (60 mL) solution containing methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-mercapto-3-methylbutanoate (as described above) (1.51 g, 5.73 mmol, 1.0 eq) was added sodium tert-butoxide (716 mg, 7.45 mmol, 1.3 eq). The resulting pale yellow mixture was allowed to stir at RT for 10 min at which time 1-(3-chloropropyl)-4-fluorobenzene (as described above) (1.09 g, 6.3 mmol, 1.1 eq) was added. The resulting solution was allowed to stir at RT for 18 hr. The reaction was then quenched with a sat NH4Cl solution, poured into H2O, and extracted (2×) with EtOAc. The combined extracts were dried over MgSO4 and concentrated in vacuo and then purified via flash chromatography using 5:1 hexanes/EtOAc as the mobile phase. Isolated 700 mg (1.75 mmol, 31% yield).

Workup

  1. additionwas added
  2. customThe reaction was then quenched with a sat NH4Cl solution
  3. additionpoured into H2O
  4. extractionextracted (2×) with EtOAc
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. custompurified via flash chromatography
  8. customIsolated 700 mg (1.75 mmol, 31% yield)

Sources & evidence

ORD record
ord-663b076e736649f589670a52b170e71b
Source dataset
uspto-grants-2006_11
Patent number
US07132443B2

Reaction notes

Loading…