Pyridine → HCID 86659594, compound

HRID 451315Notes

Reaction equation

HRID 451315 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([O:7][C:8](Cl)=[S:9])=[CH:3][CH:2]=1.N1[CH:16]=[CH:15][CH:14]=CC=1.[OH:17][N:18]1[C:24](=[O:25])[N:23]2[CH2:26][C@H:19]1[CH2:20][CH2:21][C@H:22]2[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38]CCCC)=[O:37])[CH2:32][CH2:31]1)=[O:28].Cl[CH2:44]Cl>>[O:25]=[C:24]1[N:23]2[CH2:26][C@@H:19]([CH2:20][CH2:21][C@H:22]2[C:27]([NH:29][CH:30]2[CH2:35][CH2:34][N:33]([C:36]([O:38][C:15]([CH3:14])([CH3:16])[CH3:44])=[O:37])[CH2:32][CH2:31]2)=[O:28])[N:18]1[O:17][C:8]([O:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)=[S:9]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane2×HCID 70498Phenyl thioxochloroformateHCID 131730714HCID 131730714, compound

Product 1

HCID 86659594HCID 86659594, compound

Procedure

A solution phenyl chlorothionocarbonate (1.25 eq.) in dichloromethane is added to a solution of pyridine (1.25 eq.), 4-dimethylaminoppidine (0.1 eq.) and tort-butyl 4-({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)piperidine-1-carboxylate (see Example 1, Step 2) in dichloromethane. The resulting mixture is stirred at room temperature overnight then cooled in an ice bath and quenched by addition of water. The layers are separated and the aqueous layer is extracted with dichloromethane. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under vacuum. The residue is purified by silica gel chromatography to afford the title compound.

Workup

  1. temperaturethen cooled in an ice bath
  2. customquenched by addition of water
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with dichloromethane
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-6527e579f682460897f39b79bbabf930
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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