HCID 18104467, compound → HCID 22881832, compound

HRID 481930Notes

Reaction equation

HRID 481930 reaction equation
C[O:2][C:3](=O)[C@H:4]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[NH:5][C:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[H-].C([Al+]CC(C)C)C(C)C>COCCOC.C1(C)C=CC=CC=1>[CH:8]1([C:6]([NH:5][C@H:4]([CH:3]=[O:2])[CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:7])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 18104467HCID 18104467, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22881832HCID 22881832, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-70 °C

Procedure

N-Cyclohexanoylphenylalanine methyl ester (0.5 g) was dissolved in ethylene glycol dimethyl ether (20 mL). The solution was cooled to -70° C. and diisobutylaluminum hydride (2.04 mL of a 1.5M solution in toluene) was added. The resulting reaction mixture was stirred at -70° C. for 2 hours. The reaction was quenched by dropwise addition of 2N hydrochloric acid. The mixture was extracted with cold ethyl acetate. The ethyl acetate solution was washed with brine and dried over sodium sulfate. Concentration in vacuo furnished a white solid which was purified by silica gel chromatography. Mass Spec.: M+1 m/e 261.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched by dropwise addition of 2N hydrochloric acid
  3. extractionThe mixture was extracted with cold ethyl acetate
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration in vacuo
  7. customfurnished a white solid which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-1f93dda954dd46559c5334ab14a72ff7
Source dataset
uspto-grants-1998_08
Patent number
US05792451

Reaction notes

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