Phenethyl bromide → HCID 86760293, compound

HRID 719668Notes

Reaction equation

HRID 719668 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+].Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CC#N>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([CH3:16])([S:17][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:15])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 15225634HCID 15225634, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 86760293HCID 86760293, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a CH3CN (50 mL) solution containing methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-mercapto-3-methylbutanoate (as described above) (1.26 g, 4.78 mmol, 1.0 eq) was added sodium tert-butoxide (597 mg, 6.21 mmol, 1.3 eq). The resulting pale yellow mixture was allowed to stir at RT for 10 min at which time (2-bromoethyl)benzene (718 μL, 5.26 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. Combined extracts were dried over MgSO4 and concentrated in vacuo. Purified via flash chromatography using 5:1 hexanes/EtOAc as the mobile phase. Isolated 761 mg (2.07 mmol, 45% 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 materialCombined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurified via flash chromatography
  8. customIsolated 761 mg (2.07 mmol, 45% yield)

Sources & evidence

ORD record
ord-221b6504750346e2862ecea82c28b122
Source dataset
uspto-grants-2006_11
Patent number
US07132443B2

Reaction notes

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