Ammonium Chloride → HCID 86667895, compound

HRID 335648Notes

Reaction equation

HRID 335648 reaction equation
C([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1([S:9][S:10][CH:11]2[CH2:13][CH2:12]2)[CH2:8][CH2:7]1.Br[CH2:15][C@@H:16]1[CH2:20][O:19][C:18]([CH3:22])([CH3:21])[O:17]1.[Cl-].[NH4+]>C1COCC1>[CH3:21][C:18]1([CH3:22])[O:17][C@H:16]([CH2:15][C:6]2([S:9][S:10][C:11]3([CH2:15][C@@H:16]4[CH2:20][O:19][C:3]([CH3:4])([CH3:2])[O:17]4)[CH2:13][CH2:12]3)[CH2:8][CH2:7]2)[CH2:20][O:19]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 228316552,2-Dimethyl-4(S)-4-bromomethyl-1,3-dioxalaneHCID 442285261,1'-DisulfanediyldicyclopropaneHCID 178418339Butyllithium

Product 1

HCID 86667895HCID 86667895, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyl lithium (1.7 M in hexane, 1.2 eq) is added dropwise over 1 hour to a solution of 1,2-dicyclopropyldisulfane (1 eq) in THF (1.5 mL/mmol), at −20° C. (S)-4-(bromomethyl)-2,2-dimethyl-1,3-dioxolane (1.1 eq) is then added at −78° C. and stiffing at −78° C. continued for an additional 4 hours. Saturated aqueous ammonium chloride solution is added and the mixture is extracted with ethyl acetate (3×). The combined organic extracts are dried (Na2SO4) and purified by flash chromatography (ethyl acetate in hexane eluant).

Workup

  1. additionis then added at −78° C.
  2. customstiffing at −78° C.
  3. extractionthe mixture is extracted with ethyl acetate (3×)
  4. dry with materialThe combined organic extracts are dried (Na2SO4)
  5. custompurified by flash chromatography (ethyl acetate in hexane eluant)

Sources & evidence

ORD record
ord-6b9d55164d5c4eeaa086924e79206dc0
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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