Triethylamine → tert-butyl(2S,3S)-2-(2,4-dioxo-1-imidazolidinyl)-3-methylpentanoate

HRID 1174181Notes

Reaction equation

HRID 1174181 reaction equation
[NH2:1][C:2]([N:4]([CH2:17][C:18]([O:20]CC)=O)[C@@H:5]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[O:3].C(N(CC)CC)C>CO>[O:3]=[C:2]1[NH:1][C:18](=[O:20])[CH2:17][N:4]1[C@@H:5]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86598806HCID 86598806, compound

Product 1

HCID 66891458tert-butyl(2S,3S)-2-(2,4-dioxo-1-imidazolidinyl)-3-methylpentanoateYield 47%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A solution containing the product from Example 36B (6.8 g, 20.9 mmol) in methanol (30 mL) was treated with triethylamine (5.6 mL, 40.2 mmol), stirred at 50° C. for 2 hours, and concentrated. The residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane to give the title compound (2.53 g, 47% yield).

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed on silica gel eluting with 0-30% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-830d88b1bc6d4459b2eb0752a494f9c2
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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