L-Valine → HCID 36689750, compound

HRID 1243280Notes

Reaction equation

HRID 1243280 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:15]([O:19][C:20](Cl)=[O:21])[CH:16]([CH3:18])[CH3:17]>O.O1CCOCC1>[CH2:15]([O:19][C:20]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:21])[CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 6287L-ValineHCID 10340Sodium CarbonateHCID 62365Isobutyl chloroformate

Product 1

HCID 36689750HCID 36689750, compoundYield 132%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

L-Valine (5.86 g, 50 mmol) was dissolved in a mixture of water (200 mL) containing sodium carbonate (10.6 g, 100 mmol). The solution was cooled to 0° C., then a solution of isobutylchloroformate (6.76 g, 49.5 mmol) in dioxane (100 mL) was added dropwise over 50 min. The ice-bath was removed and the reaction stirred overnight. Dioxane was evaporated, the aqueous phase was extracted once with diethylether and the brought to pH 2 by addition of hydrochloric acid. Extraction with DCM (3×, 150 mL each), drying of the organic phase (sodium sulfate) and evaporation gave 21 (14.2 g) as a colorless solid. 1H-NMR (DMSO-d6) δ 12.48 (bs, 1 H), 7.24 (d, J=8.2 Hz, 1 H), 3.95 (dd, J=6.2, 8.3 Hz, 1 H), 3.73 (d, J=6.7 Hz, 1 H), 2.01 (m, 1 H), 1.83 (m, 1 H), 0.87 (bs, 12 H).

Workup

  1. customThe ice-bath was removed
  2. customDioxane was evaporated
  3. extractionthe aqueous phase was extracted once with diethylether
  4. additionthe brought to pH 2 by addition of hydrochloric acid
  5. extractionExtraction with DCM (3×, 150 mL each)
  6. dry with materialdrying of the organic phase (sodium sulfate) and evaporation

Sources & evidence

ORD record
ord-2f1ccc43c400479b85f22958de4ef8bd
Source dataset
uspto-grants-2006_10
Patent number
US07119073B2

Reaction notes

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