Diisopropylcarbodiimide → HCID 70146440, compound

HRID 2303755Notes

Reaction equation

HRID 2303755 reaction equation
[C:1]([NH:11][C:12]1[CH:17]=[CH:16][N:15]([CH2:18][C:19]([OH:21])=O)[C:14](=[O:22])[N:13]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(C)N=C=NC(C)C.[NH:32]1[CH2:37][CH2:36][NH:35][CH2:34][C:33]1=[O:38]>C1C=CC=CC=1>[C:1]([NH:11][C:12]1[CH:17]=[CH:16][N:15]([CH2:18][C:19]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][C:33]2=[O:38])=[O:21])[C:14](=[O:22])[N:13]=1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 231360Piperazin-2-oneHCID 7254702-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid

Product 1

HCID 70146440HCID 70146440, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(N4-CBz-cytosin-1-yl)acetic acid (2.42 g, 8 mmol) was azeotroped with benzene (3×25 mL) and dried under vacuum. 32 mL of anhydrous DMF was added under N2 followed by the addition of DIC (1.57 mL, 8 mmol). The reaction was stirred at room temperature for 2-3 minutes, then treated with piperazinone (8.8 mmol, 881.1 mg), and the reaction mixture was left to stir for 48 hours. The reaction mixture was concentrated by rotary evaporation, washed successively with 0.1 N citric acid solution (2×10 mL) and water (2×15 mL), and then dried in a dessicator, affording N-[(N4-CBz-cytosin-1-yl)acetyl]-piperazinone as a white solid.

Workup

  1. customdried under vacuum
  2. addition32 mL of anhydrous DMF was added under N2
  3. waitthe reaction mixture was left
  4. stirringto stir for 48 hours
  5. concentrationThe reaction mixture was concentrated by rotary evaporation
  6. washwashed successively with 0.1 N citric acid solution (2×10 mL) and water (2×15 mL)
  7. customdried in a dessicator

Sources & evidence

ORD record
ord-5334bbbbcff343caaf2cac654c974d49
Source dataset
uspto-grants-2002_08
Patent number
US06433134B1

Reaction notes

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