Methyl chloroformate → HCID 123665052, compound

HRID 923468Notes

Reaction equation

HRID 923468 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@:8]([NH:19][S@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH3:18])[CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.CCCCCC.Cl[C:38]([O:40][CH3:41])=[O:39].[Cl-].[NH4+]>C1COCC1>[CH3:15][C:14]([CH3:17])([Si:11]([CH3:13])([CH3:12])[O:10][CH2:9][C@:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:38]([O:40][CH3:41])=[O:39])([CH3:18])[NH:19][S@@:20](=[O:21])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:16]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 123149100HCID 123149100, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 123665052HCID 123665052, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 403 mg of (S)—N-[(2R)-2-(3-bromophenyl)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-yl]-2-methylpropane-2-sulfinamide in 4 ml of THF was added 1.4 ml of a 1.63 M n-butyllithium/hexane solution at −78° C., followed by stirring for 30 minutes, and then 283 μl of methyl chloroformate was added dropwise thereto, followed by stirring for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 280 mg of methyl 3-[(6R,8S)-2,2,3,3,6,9,9-heptamethyl-8-oxo-4-oxa-8λ4-thia-7-aza-3-siladecan-6-yl]benzoate.

Workup

  1. stirringby stirring for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bdbeda83e1e54ac1a23d84e2e35117a2
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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