Hydrochloric Acid → 2-(2-Oxopyrrolidin-1-yl)acetic acid

HRID 1711130Notes

Reaction equation

HRID 1711130 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].Cl.[OH-].[Na+].[CH2:12]1COC[CH2:13]1>CO.C(Cl)Cl>[O:3]=[C:1]1[CH2:2][CH2:13][CH2:12][N:4]1[CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10972AcetylglycineHCID 20445995Sodium hydroxide tetrahydrofuran

Product 1

HCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
50 °C

Procedure

N-Acetylglycine (0.031 ml, 0.22 mmol) was dissolved in 1:1 10N NaOH/THF (2 ml) and was stirred at 50° C. for 1 h. The mixture was neutralized to pH 4 with 6N HCl, then concentrated. The yellowish solid was diluted with 1:1 MeOH/CH2Cl2 (25 ml), filtered to remove inorganic salts, and concentrated. The solid obtained was diluted again with 1:1 MeOH/CH2Cl2 and concentrated to give (2-oxo-pyrrolidin-1-yl)-acetic acid as a white solid. The crude product was used in the next reaction without purification.

Workup

  1. concentrationconcentrated
  2. additionThe yellowish solid was diluted with 1:1 MeOH/CH2Cl2 (25 ml)
  3. filtrationfiltered
  4. customto remove inorganic salts
  5. concentrationconcentrated
  6. customThe solid obtained
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-94990eed217c48319986390f1a76d9ed
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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