Ammonium Chloride → HCID 70235472, compound

HRID 1387469Notes

Reaction equation

HRID 1387469 reaction equation
[CH2:1]([NH:8][C@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:22]([O:26][C:27](=[O:41])[CH:28]=[CH:29][C:30]1[CH:39]=[C:38]2[C:33]([O:34][CH2:35][C:36](=[O:40])[NH:37]2)=[N:32][CH:31]=1)([CH3:25])([CH3:24])[CH3:23].[NH4+].[Cl-]>C1COCC1>[C:22]([O:26][C:27](=[O:41])[CH2:28][C@H:29]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[C:30]1[CH:39]=[C:38]2[C:33]([O:34][CH2:35][C:36](=[O:40])[NH:37]2)=[N:32][CH:31]=1)([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 1268086(+)-BenzylphenethylamineHCID 54022061HCID 54022061, compoundHCID 178418339Butyllithium

Product 1

HCID 70235472HCID 70235472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of N-benzyl-α-(R)-methylbenzylamine (0.82 g, 3.87 mmol) in THF (25 mL) at 0° C. was treated with n-BuLi (1.6 mL of a 2.5 M soln in hexanes). The resulting solution was stirred at 0° C. for 30 min and then cooled to −78° C. A solution of acrylate 20-5 (0.485 g, 1.76 mmol) in THF (5 mL) was added. After stirring for 15 min at −78° C., satd aq NH4Cl soln (5 mL) was added and the cold bath removed. The mixture was warmed to room temperature, and extracted with Et2O (2×40 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4, filtered, and concentrated. The residue was purified by flash chromatography (40% ethyl acetate/hexanes) to give the β-aminoester 20-6 as a yellow oil.

Workup

  1. temperaturecooled to −78° C
  2. stirringAfter stirring for 15 min at −78° C.
  3. additionwas added
  4. customthe cold bath removed
  5. temperatureThe mixture was warmed to room temperature
  6. extractionextracted with Et2O (2×40 mL)
  7. washThe combined organic extracts were washed with brine (30 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by flash chromatography (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-378a6ad6bfbe4272a122b5d54464ce47
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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