N-Hydroxysuccinimide → 1-Pyrrolidineacetamide, 3-hydroxy-2-oxo-, (+-)-

HRID 1087081Notes

Reaction equation

HRID 1087081 reaction equation
C([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11](O)=[O:12])[C:6]1=[O:14])(=O)C.O[N:16]1C(=O)CCC1=O>C(Cl)(Cl)Cl>[OH:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH2:16])=[O:12])[C:6]1=[O:14]

Participants

4

Reactant 2

HCID 80170N-HydroxysuccinimideHCID 54389912(R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid

Product 1

HCID 30698541-Pyrrolidineacetamide, 3-hydroxy-2-oxo-, (+-)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1.64 g of dicyclohexylcarbondiimide dissolved in 20 ml of chloroform are added at room temperature to 1.5 g of (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid, 40 ml of chloroform and 0.86 g of N-hydroxysuccinimide. After 4 hours, the solid is filtered, whereupon the filtrate is concentrated and again filtered. The filtrate is evaporated. The residue is treated at room temperature with 40 ml of a saturated solution of ammonia in methanol. The mixture is stirred at room temperature for 5 minutes, 10 ml of ion-free water are then added thereto and the mixture is stirred at room temperature for an additional minutes. The precipitated solid is filtererd. The filtrate is evaporated, the residue is stirred in 30 ml of acetonitrile and the crystallized-out product is recrystallized two more times from acetonitrile. There is obtained (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide of melting point 162°-164°.

Workup

  1. filtrationthe solid is filtered, whereupon the filtrate
  2. concentrationis concentrated
  3. filtrationagain filtered
  4. customThe filtrate is evaporated
  5. additionThe residue is treated at room temperature with 40 ml of a saturated solution of ammonia in methanol
  6. addition10 ml of ion-free water are then added
  7. stirringthe mixture is stirred at room temperature for an additional minutes
  8. customThe filtrate is evaporated
  9. stirringthe residue is stirred in 30 ml of acetonitrile
  10. customthe crystallized-out product is recrystallized two more times from acetonitrile

Sources & evidence

ORD record
ord-fc2f752920dc44559c6f5dce9685f062
Source dataset
uspto-grants-1991_07
Patent number
US05034402

Reaction notes

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