Acetic Acid → N-Acetyl-L-proline

HRID 538952

Reaction equation

[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[C:9](O)(=[O:11])[CH3:10]>>[C:9]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])(=[O:11])[CH3:10]

Participants

Reactant 2

HCID 176Acetic Acid

HCID 145742L-Proline

Product 1

HCID 66141N-Acetyl-L-prolineYield 82.5%

Conditions

Temperature: 150 °C

Procedure

Proline (1 g, 8.68 mmol) and acetic acid (20 mL) were mixed together and heated at 150° C. in a microwave for two hours. The excess acetic acid was removed using a rotary evaporator. The residue was stirred in MTBE at ambient temperature until a solid precipitated. The mixture was filtered and the solid was washed with MTBE. The solid was dried in a vacuum oven at 60° C. The product was obtained as a white solid (1.12 g, 82.5%). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.77-1.95 (m, 4H), 1.97 (s, 2H), 2.0-2.19 (m, 1H), 3.35 (dt, 1H), 3.41-3.58 (m, 2H), 4.19 (dd, 1H).

Workup

customThe excess acetic acid was removed
customa rotary evaporator
customprecipitated
filtrationThe mixture was filtered
washthe solid was washed with MTBE
customThe solid was dried in a vacuum oven at 60° C

Sources & evidence

ORD record: ord-6ed644f87871434daf97c199c235ef07
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865920B2

Linked notes

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