Acetyl chloride → L-Norvaline, methyl ester

HRID 863187

Reaction equation

HRID 863187 reaction equation
[C:1](Cl)(=O)C.[NH2:5][C@H:6]([C:10]([OH:12])=[O:11])[CH2:7][CH2:8][CH3:9]>CO>[CH3:1][O:11][C:10](=[O:12])[C@H:6]([CH2:7][CH2:8][CH3:9])[NH2:5]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 65098L-Norvaline

Product 1

HCID 7019097L-Norvaline, methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 20 mL of methanol was slowly added 2.6 mL acetyl chloride. Then 2.0 g (17.1 mmole) of L-norvaline was added. The solution was heated to reflux and monitored by thin-layer chromatography (TLC) until complete. The methanol was stripped off by rotary evaporation and the resulting oil was pumped under high vacuum overnight to give the title compound. NMR(300 MHZ, CD3OD): δ 4.03 (t, Nva-α, 1H), 3.81 (s, COOCH3, 3H), 1.87 (m, CH2CH2CH3, 2H), 1.44 (m, CH2CH2CH3, 2H), 0.98 (t, CH2CH2CH3, 3H).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. customThe methanol was stripped off by rotary evaporation
  4. customwas pumped under high vacuum overnight

Sources & evidence

ORD record
ord-d038bcdebc68470bb7cdd8f58e0a9df3
Source dataset
uspto-grants-1998_02
Patent number
US05719296

Linked notes

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