Pyridine → HCID 22928306, compound

HRID 720040Notes

Reaction equation

HRID 720040 reaction equation
C1N=CN([C:6](N2C=NC=C2)=[O:7])C=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1.C(Cl)Cl>[NH:18]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:6][O:7][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:19]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 22928306HCID 22928306, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the Wang resin (12 g, 1.1 mmol/g) in a 250 mL peptide synthesis vessel was added 120 mL of 0.4 N CDI in anhydrous THF, and shaken at room temperature for 17 hours. The resin was thoroughly washed with CH2Cl2 (3×100 mL ) and THF (3×100 mL) to remove the excess CDI and then treated with 120 mL of 0.4 N 3-piperidinemethanol in THF at room temperature for 17 hours. The resulting resin 1 was washed with DMF (3×100 mL), MeOH (4×100 mL), and CH2Cl2 (4×100 mL) and dried in vacuo. To the alcohol resin 1 was added methanesulfonyl chloride (5.11 ml, 66 mmol) in 100 mL CH2Cl2 followed by 20 mL of pyridine, and the resulting slurry was shaken at room temperature for 17 hours. The resulting mesylate resin 2 was washed with DMF (3×100 mL), MeOH (4×100 mL), and CH2Cl2 (4×100 mL) and dried in vacuo.

Workup

  1. washThe resin was thoroughly washed with CH2Cl2 (3×100 mL ) and THF (3×100 mL)
  2. customto remove the excess CDI
  3. additiontreated with 120 mL of 0.4 N 3-piperidinemethanol in THF at room temperature for 17 hours
  4. washThe resulting resin 1 was washed with DMF (3×100 mL), MeOH (4×100 mL), and CH2Cl2 (4×100 mL)
  5. customdried in vacuo
  6. stirringthe resulting slurry was shaken at room temperature for 17 hours
  7. washThe resulting mesylate resin 2 was washed with DMF (3×100 mL), MeOH (4×100 mL), and CH2Cl2 (4×100 mL)
  8. customdried in vacuo

Sources & evidence

ORD record
ord-f7541e8b395a471ca1d08c86c8bf08c9
Source dataset
uspto-grants-2006_11
Patent number
US07132551B2

Reaction notes

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