Chlorosuccinimide → HCID 89526536, compound

HRID 2278342Notes

Reaction equation

HRID 2278342 reaction equation
[Si:1]([O:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18](CCC(OC)=O)(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[O-].[Na+].C1C(=O)N([Cl:37])C(=O)C1>C1COCC1>[Si:1]([O:8][CH:9]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([Cl:37])(=[O:20])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 10942334Sodium MethoxideHCID 131733451HCID 131733451, compound

Product 1

HCID 89526536HCID 89526536, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-[(1-{[tert-butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-5-yl)sulfonyl]propanoate (140 mg, 0.35 mmol) in THF (1 mL) was added sodium methoxide (0.70 mL, 0.5 M, 0.35 mmol). The reaction mixture was stirred for 20 minutes, then the solvents were removed under reduced pressure and the residue was stripped down from heptanes to generate a white foam. This foam was suspended in DCM (2 mL) at 0° C. and then NCS (47 mg, 0.35 mmol) was added and the reaction mixture was stirred for 1 hour. The reaction was quenched by the addition of brine (2 mL) and the phases were separated using a phase separator. The aqueous layer washed with DCM, and the combined organic layers were concentrated under reduced pressure. The crude concentrate was purified on silica gel eluting with hexanes and ethyl acetate to afford the title compound.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customwas suspended in DCM (2 mL) at 0° C.
  3. stirringthe reaction mixture was stirred for 1 hour
  4. customThe reaction was quenched by the addition of brine (2 mL)
  5. customthe phases were separated
  6. washThe aqueous layer washed with DCM
  7. concentrationthe combined organic layers were concentrated under reduced pressure
  8. concentrationThe crude concentrate
  9. customwas purified on silica gel eluting with hexanes and ethyl acetate

Sources & evidence

ORD record
ord-5dc29513d66e4b4180e4ce88feea0ab3
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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