Hydrochloric Acid → HCID 86601530, compound

HRID 1432520Notes

Reaction equation

HRID 1432520 reaction equation
[C:1]([NH:8][C@@H:9]([C:13]([N:15]1[CH2:20][CH:19]=[CH:18][CH:17]([OH:21])[CH2:16]1)=[O:14])[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1>[S:23]([O:21][CH:17]1[CH:18]=[CH:19][CH2:20][N:15]([C:13](=[O:14])[C@@H:9]([CH:10]([CH3:12])[CH3:11])[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:16]1)([CH3:22])(=[O:25])=[O:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 68952121HCID 68952121, compound

Product 1

HCID 86601530HCID 86601530, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

0.894 g of N—(N-BOC-(R)-valyl)-1,2,3,6-tetrahydropyridin-3-ol dissolved in 10 ml of CH2Cl2 are treated with 0.844 g of 4-dimethylaminopyridine and 0.31 g of methanesulfonic acid chlorid (mesylchloride) and stirred for ca. 24 hours, the mixture obtained is treated with 0.1 N HCl and CH2Cl2, the organic phase obtained is washed with H2O and aqueous NaHCO3-solution, the solvent is evaporated and the evaporation residue is dried. 3-Mesyloxy-N—(N-BOC-(R)-valyl)-1,2,3,6-tetrahydropyridine is obtained. 1H-NMR (CDCl3): 6.1-5.85(m,2H,HIV,HV), 4.5(m,1H,NHCHCO), 3.7(s,3H,CH3SO2), 1.2-0.9(m,6H,(CH3)2.

Workup

  1. customthe mixture obtained
  2. customthe organic phase obtained
  3. washis washed with H2O and aqueous NaHCO3-solution
  4. customthe solvent is evaporated
  5. customthe evaporation residue is dried

Sources & evidence

ORD record
ord-64b10d009dd6466ea8d332cd6ed18b44
Source dataset
uspto-grants-2009_11
Patent number
US07612103B2

Reaction notes

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