Sodium hydrogen sulphide → HCID 86660746, compound

HRID 932244Notes

Reaction equation

HRID 932244 reaction equation
[CH3:1][S:2]([O-])(=O)=O.[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N+:11]2[C@@H:29]([CH:32]3[CH2:34][CH2:33]3)C[O:31][C:10]1=2)[CH:7]=[CH2:8].S.[Na]>CN(C=O)C>[CH2:6]([C@@:9]1([CH3:35])[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)[C@@H:12]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[N:11]([C@@H:29]([CH:32]2[CH2:34][CH2:33]2)[CH2:1][SH:2])[C:10]1=[O:31])[CH:7]=[CH2:8]

Participants

4

Reactant 2

HCID 86586439Sodium hydrogen sulphideHCID 86660743HCID 86660743, compound

Product 1

HCID 86660746HCID 86660746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S,5S,6R,8S)-8-allyl-6-(3-chlorophenyl)-5-(4-chlorophenyl)-3-cyclopropyl-8-methyl-2,3,5,6,7,8-hexahydrooxazolo[3,2-a]pyridin-4-ium methanesulfonate (370 mg; Example 349, Step A) in DMF (1.6 mL) was added sodium hydrogensulfide (105 mg, 1.88 mmol). After being stirred at rt overnight, the reaction was quenched (sat. aq. NH4Cl solution), extracted (2×EtOAc) and the combined organics were washed with brine (3×). The combined organic layers were dried (Na2SO4) and concentrated under the reduced pressure. Purification of the residue by chromatography on silica gel (24 g SiO2, gradient elution of 10% to 40% EtOAc in hex) provided the title compound.

Workup

  1. customthe reaction was quenched (sat. aq. NH4Cl solution)
  2. extractionextracted (2×EtOAc)
  3. washthe combined organics were washed with brine (3×)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under the reduced pressure
  6. customPurification of the residue by chromatography on silica gel (24 g SiO2, gradient elution of 10% to 40% EtOAc in hex)

Sources & evidence

ORD record
ord-93aeb5a363d94595ae08c2c09cbb637f
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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