Chloroform → HCID 69100830, compound

HRID 394038Notes

Reaction equation

HRID 394038 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][NH:10][C:11]([C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([C@@H:20]2[CH2:24][C@@H:23]([OH:25])[CH2:22][N:21]2[C:26](=[O:47])[CH2:27][C:28]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:19])=[O:12])[CH2:4]1)[CH3:2].[CH2:48](I)[CH3:49].C(Cl)(Cl)[Cl:52]>>[Cl-:52].[CH2:1]([N+:3]1([CH2:48][CH3:49])[CH2:8][CH2:7][CH2:6][C@@H:5]([CH2:9][NH:10][C:11]([C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([C@@H:20]2[CH2:24][C@@H:23]([OH:25])[CH2:22][N:21]2[C:26](=[O:47])[CH2:27][C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:19])=[O:12])[CH2:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 6340IodoethaneHCID 69100640HCID 69100640, compound

Product 1

HCID 69100830HCID 69100830, compound

Conditions

Temperature
70 °C

Procedure

To 22 mg of (2R)-N-{((3S)-1-ethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxamide, 1 ml of ethyl iodide was added at room temperature, followed by 2 hours' stirring at 70° C. The resultant reaction liquid was diluted with chloroform and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in ultrapure water 0.6 ml/methanol 0.1 ml and the solution was developed on reversed phase medium-pressure liquid chromatograpy [ODS-AQ 120-S50 (YMC)]. Purification and anion exchange were conducted by pouring 20 ml of saturated brine, washing with 150 ml of ultrapure water and eluting the title compound with methanol/water=1/1, to provide 21 mg of the title compound as a white solid.

Workup

  1. customThe resultant reaction liquid
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe resultant residue was dissolved in ultrapure water 0.6 ml/methanol 0.1 ml
  4. customPurification and anion exchange
  5. additionby pouring 20 ml of saturated brine
  6. washwashing with 150 ml of ultrapure water
  7. washeluting the title compound with methanol/water=1/1

Sources & evidence

ORD record
ord-e54de950ac4f47c7a655ec69d97bb060
Source dataset
uspto-grants-2004_10
Patent number
US06809108B1

Reaction notes

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