1-Acetyl-4-hydroxypyrrolidine-2-carboxylic acid → Diisopropylcarbodiimide

HRID 1271529Notes

Reaction equation

HRID 1271529 reaction equation
NC(C([C:12]1S[C:14]2C=CC=[CH:17][C:15]=2[N:16]=1)=O)CCCNC(N)=N.C([N:24]1CC(O)[CH2:26][CH:25]1[C:30](O)=O)(=O)C>C1COCC1.O>[CH:25]([N:24]=[C:12]=[N:16][CH:15]([CH3:14])[CH3:17])([CH3:30])[CH3:26]

Participants

5

Reactant 2

HCID 5383411-Acetyl-4-hydroxypyrrolidine-2-carboxylic acidHCID 178512951HCID 178512951, compound

Product 1

HCID 12734Diisopropylcarbodiimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solid mixture of N-(4-amino-5-benzothiazol-2-yl-5-oxo-pentyl)-guanidine (0.24 g, 0.83 mmol) and 1-acetyl-4-hydroxy-pyrrolidine-2-carboxylic acid (0.14 g, 0.83 mmol) was dissolved in THF (10 mL) and water (2 mL). To the reaction mixture was then added N,N′-diisopropyl carbodiimide to yield a reaction mixture of pH 1.8 at 0° C. The pH of the reaction mixture was adjusted to about 5.5 with 8% NaHCO3. The reaction mixture was stirred at ambient temperature for 4 hours. The title compound was detected by HPLC (180 mg) and assayed by weight analysis.

Sources & evidence

ORD record
ord-cb3b725fe2764ff49a54c5b6d82bd1df
Source dataset
uspto-grants-2007_04
Patent number
US07205384B2

Reaction notes

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