Triethylamine → HCID 86607766, compound

HRID 854274Notes

Reaction equation

HRID 854274 reaction equation
[NH2:1][C@H:2]([CH3:22])[CH2:3][CH2:4][N:5]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C@@H:6]([C:8](OC)=[O:9])[CH3:7].C[Al](C)C.C(N(CC)CC)C>ClCCl>[CH3:7][C@@H:6]1[C:8](=[O:9])[NH:1][C@H:2]([CH3:22])[CH2:3][CH2:4][N:5]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16682925TrimethylaluminumHCID 69154974HCID 69154974, compound

Product 1

HCID 86607766HCID 86607766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl N-[(3R)-3-aminobutyl]-N-[(benzyloxy)carbonyl]-D-alaninate (0.5 g, 1.6 mmol) in dichloromethane (65 mL) was added trimethylaluminum (0.8 mL, 2M in toluene) and triethylamine (0.025 mL, 0.16 mmol), and the reaction mixture was stirred overnight at room temperature. Celite was added and the reaction was quenched by the dropwise addition of saturated aqueous ammonium chloride solution. The white granular solid formed was filtered and washed with dichloromethane. The filtrate was evaporated and purified by flash chromatography on a Biotage® system (silica gel, 5% methanol/dichloromethane) to yield the title compound. MS 277.2 (M+1).

Workup

  1. additionCelite was added
  2. customthe reaction was quenched by the dropwise addition of saturated aqueous ammonium chloride solution
  3. customThe white granular solid formed
  4. filtrationwas filtered
  5. washwashed with dichloromethane
  6. customThe filtrate was evaporated
  7. custompurified by flash chromatography on a Biotage® system (silica gel, 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-24bbb9c9858348ffa78fc65b5669bc28
Source dataset
uspto-grants-2007_08
Patent number
US07259160B2

Reaction notes

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