Pyrrolidone carboxylic acid → HCID 68665397, compound

HRID 1443404Notes

Reaction equation

HRID 1443404 reaction equation
[NH:1]1[CH:5]([C:6](O)=O)[CH2:4][CH2:3][C:2]1=[O:9].[CH3:10][C:11]1[CH:16]=C[CH:14]=[CH:13][C:12]=1[O:17][CH3:18].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O>C(Cl)Cl.O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][C:6]([CH:5]2[NH:1][C:2](=[O:9])[CH2:3][CH2:4]2)=[CH:10][C:11]=1[CH3:16]

Participants

7

Reactant 4

HCID 499Pyrrolidone carboxylic acidHCID 6395Methanesulfonic AcidHCID 14812Phosphorus oxide (P4O10)HCID 336372-Methylanisole

Product 1

HCID 68665397HCID 68665397, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Pyrrolidone-5-carboxylic acid (2.0 g, 15.5 mmol) and 2-methylanisole (2.1 mL, 17.0 mmol) were added to a mixture of 1.0 g (3.52 mmol) of phosphorous pentoxide and 6.7 mL methanesulfonic acid. The mixture was heated at 100° C. for 2 hr, cooled down to rt, and poured into a mixture of H2O and CH2Cl2. The aqueous layer was separated, and extracted with CH2Cl2 (3×20 mL). Organic layers were combined, washed with sat'd NaHCO3, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 4:1 v/v EtOAc/hexanes as the eluant afforded 1.78 g (56%) of the title compound: 1H NMR δ 1.88-1.97 (m, 1H), 2.21 (s, 3H), 2.35-2.54 (m, 3H), 3.81 (s, 3H), 4.66 (t, J=7.1, 1H), 6.53 (br. s, 1H), 6.79 (d, J=8.6, 1H), 7.05-7.09 (m, 2H).

Workup

  1. temperaturecooled down to rt
  2. customThe aqueous layer was separated
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. washwashed with sat'd NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef0c08fd55f84059a40b2a575c485751
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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