Cyclopentanecarboxylic acid → HCID 21760921, compound

HRID 1742060Notes

Reaction equation

HRID 1742060 reaction equation
[C:1]([NH:5][C:6]1[CH:32]=[CH:31][C:9]([CH2:10][CH2:11][N:12]2[C:20]3[N:19]=[C:18]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[NH:17][C:16]=3[C:15](=[O:26])[N:14]([CH2:27][CH2:28][CH3:29])[C:13]2=[O:30])=[CH:8][CH:7]=1)(=[O:4])[CH2:2][CH3:3].[CH:33]1(C(O)=O)[CH2:37]CC[CH2:34]1.[O:41]1CCOCC1>O>[NH2:19][C:20]1[N:12]([CH2:11][CH2:10][C:9]2[CH:31]=[CH:32][C:6]([NH:5][C:1]([CH:2]3[CH2:37][CH2:33][CH2:34][CH2:3]3)=[O:4])=[CH:7][CH:8]=2)[C:13](=[O:30])[N:14]([CH2:27][CH2:28][CH3:29])[C:15](=[O:26])[C:16]=1[NH:17][C:18]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:41]

Participants

5

Reactant 3

HCID 18840Cyclopentanecarboxylic acidHCID 312751,4-DioxaneHCID 15235761HCID 15235761, compound

Product 1

HCID 21760921HCID 21760921, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound k obtained in Reference Example 2 (10.8 g, 35.3 mmol) was dissolved in a mixture of 100 ml of dioxane and 100 ml of water, and 3.86 ml (35.5 mmol) of cyclopentanecarboxylic acid was added to the solution. Then, 1-ethyl-3-(3-dimethylamino)propylcarbodiimide hydrochloride (11.2 g, 56.8 mmol) was added slowly at room temperature at pH 5-6 over a period of five minutes. The crystals formed were collected by filtration to give 7.13 g (yield: 41%) of 6-amino-1-[4-(cyclopentanecarbonylamino)phenethyl]-5-(cyclopentanecarbonyl) amino-3-propyluracil (Compound x) as white powder.

Workup

  1. additionwas added to the solution
  2. customThe crystals formed
  3. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-02de4641ec3c40bd9c8649b7a0692ec0
Source dataset
uspto-grants-1994_08
Patent number
US05336769

Reaction notes

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