Dicyclohexylcarbodiimide → 1,2-Pyrrolidinedicarboxylic acid, 2-(2,5-dioxo-1-pyrrolidinyl) 1-(phenylmethyl) ester, (2S)-

HRID 1789229Notes

Reaction equation

HRID 1789229 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([O:5][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])=[O:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 8534821,2-Pyrrolidinedicarboxylic acid, 2-(2,5-dioxo-1-pyrrolidinyl) 1-(phenylmethyl) ester, (2S)-

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Z-Pro (7.5 gm, 0.03 mole) and N-Hydroxysuccinimide (3.45 gm, 0.03 mole) were dissolved in cold dioxane and dicyclohexylcarbodiimide (DCC) (6.18 gm, 0.03 mole) was added with rapid stirring. The mixture was stirred overnight at room temperature and the next day the solid dicyclohexylurea (DCU) was filtered off. The solvent was removed and the oil was recrystallized from isopropyl alcohol. Crystals of Z-Pro-OSu formed with scratching. Yield 8.4 gm. Melting point 86.5°-87.5° C.

Workup

  1. filtrationthe next day the solid dicyclohexylurea (DCU) was filtered off
  2. customThe solvent was removed
  3. customthe oil was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-629bbd2014a249eeba8a9b2d984002ca
Source dataset
uspto-grants-1987_08
Patent number
US04687841

Reaction notes

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