Triethylamine → HCID 10657950, compound

HRID 565235Notes

Reaction equation

HRID 565235 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN.[CH2:20]([N:22](CC)CC)C>ClCCl>[CH3:20][NH:22][C:10](=[O:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 10657950HCID 10657950, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid (120 g, 519 mmol) in dichloromethane (800 mL) is added 1,1-carbonyldiimidazole (88.4 g, 545 mmol). The resulting solution is stirred at 25° C. for 1 h and methylamine hydrochloride (52.5 g, 779 mmol) and triethylamine (157.3 g, 1557 mmol) are added and the reaction is stirred for an additional 18 h. The mixture is diluted with dichloromethane (600 mL) and washed with 1 M hydrochloric acid and saturated aqueous sodium chloride. The organic layer is dried over anhydrous magnesium sulfate and concentrated in vacuo to provide (2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid methylamide as a white solid (126 g, 100% yield).

Workup

  1. stirringthe reaction is stirred for an additional 18 h
  2. washwashed with 1 M hydrochloric acid and saturated aqueous sodium chloride
  3. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-51357008219c4217ad8f5307783f4885
Source dataset
uspto-grants-2001_01
Patent number
US06172064B2

Reaction notes

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