Chloride → HCID 12149971, compound

HRID 272080Notes

Reaction equation

HRID 272080 reaction equation
[Cl-].[CH:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][NH:16][C:17]([C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([C@@H:26]3[CH2:30][C@@H:29]([OH:31])[CH2:28][N:27]3[C:32](=[O:53])[CH2:33][C:34]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:25])=[O:18])[CH2:10]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C>ClCCl.CS(C)=O.C(Cl)(Cl)Cl>[CH:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][NH:16][C:17]([C@H:19]3[CH2:23][CH2:22][CH2:21][N:20]3[C:24]([C@@H:26]3[CH2:30][C:29](=[O:31])[CH2:28][N:27]3[C:32](=[O:53])[CH2:33][C:34]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:25])=[O:18])[CH2:10]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 3

HCID 312ChlorideHCID 8471TriethylamineHCID 12149979HCID 12149979, compound

Product 1

HCID 12149971HCID 12149971, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.0037 ml of oxaryl chloride in 0.3 ml of dichloromethane, 0.0065 ml of dimethyl sulfoxide was added at −78° C., followed by 20 minutes' stirring at the same temperature. Then a solution of 25 mg of (2R)-N-{((3R)-1-cyclohexylmethyl-3-piperidyl)methyl}-1-{(2S,4R)-4-hydroxy-1-(3,3,3-triphenylpropanoyl)pyrrolidin-2-yl}carbonylpyrrolidine-2-carboxamide in 0.9 ml of dichloromethane was added at the same temperature, followed by 30 minutes' stirring, addition of 0.0024 ml of triethylamine at the same temperature, and 20 minutes' stirring at room temperature. The reaction liquid was diluted with chloroform, washed with saturated brine and dried over anhydrous sodium sulfate. Distilling the solvent off under reduced pressure, the resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck); chloroform/methanol=9/1), to provide 18 mg of the title compound as a pale pink solid.

Workup

  1. waitfollowed by 30 minutes
  2. stirring' stirring
  3. stirringstirring at room temperature
  4. customThe reaction liquid
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationDistilling the solvent off under reduced pressure
  8. customthe resulting residue was purified with a preparative thin-layer chromatography (Kieselgel™ 60F254, Art5744 (Merck); chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-904dc79c8ce7499c942a75f9707f25fe
Source dataset
uspto-grants-2008_11
Patent number
US07452908B2

Reaction notes

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