Sodium Chloride → HCID 54519419, compound

HRID 974176Notes

Reaction equation

HRID 974176 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8]C[C@@H](O)[C@@H:11]2[N:14]2CCC[CH2:15]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CS(Cl)(=O)=O.CN.[Cl-].[Na+].[OH-].[Na+].[CH2:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])[CH3:32]>O1CCCC1.C(O)C.O>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:32][C@@H:31]([N:33]3[CH2:36][CH2:37][CH2:35][CH2:34]3)[C@@H:11]2[NH:14][CH3:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

10

Reactant 6

HCID 5234Sodium ChlorideHCID 6329MethylamineHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 54014236HCID 54014236, compound

Product 1

HCID 54519419HCID 54519419, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Using the procedure of Step B of Example 1, 1.31 g of the product of Step A, 10 ml of tetrahydrofuran, 0.90 m of triethylamine and 0.52 ml of methanesulfonyl chloride in 1.3 ml of tetrahydrofuran which is added at -20° C. were reacted. 7 ml of methylamine in solution at 33% in ethanol were used and after 1 hour of stirring, the solvent was evaportated. 50 ml of water saturated with sodium chloride and 2 ml of sodium hydroxide at 33% were added and extraction was done with methylene chloride. The organic phase was washed with water, dried and the solvent was evaporated to obtain 1.55 g of the expected product which was crystallized from isopropanol to obtain 1.03 g of product melting at 85° C.

Workup

  1. additionis added at -20° C.
  2. customwere reacted
  3. extractionextraction
  4. washThe organic phase was washed with water
  5. customdried
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b728b9ca275f44bebb8b654dbfbcf729
Source dataset
uspto-grants-1991_11
Patent number
US05068244

Reaction notes

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