Triethylamine → HCID 57889742, compound

HRID 1820229Notes

Reaction equation

HRID 1820229 reaction equation
[NH2:1][C@H:2]([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[C:9](=O)([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[O:10]N1C(=O)CCC1=O.C(N(CC)CC)C.S([O-])(O)(=O)=O.[Na+]>O1CCOCC1.O>[CH3:7][CH:6]([CH3:8])[C@@H:2]([NH:1][C:9]([O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])=[O:10])[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 71563D-ValineHCID 516919Sodium BisulfateHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate

Product 1

HCID 57889742HCID 57889742, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of (R)-2-amino-3-methylbutanoic acid (2.01 g, 17.16 mmol) and 2,5-dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonate (4.89 g, 18.87 mmol) in 1:1 dioxane/water (40 mL) was treated with triethylamine (3.59 mL, 25.7 mmol), and the mixture was stirred for two days at room temperature. The mixture was acidified with saturated sodium hydrogen sulfate and extracted 3× with ethyl acetate. The combined organic phases were washed with saturated sodium hydrogen sulfate, water, and brine, then dried over sodium sulfate and concentrated in-vacuo to yield the title compound (4.17 g, 15.96 mmol, 93% yield) as an amber oil.

Workup

  1. extractionextracted 3× with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium hydrogen sulfate, water, and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-d2883602950e444b90fd787b96549c5a
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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