HCID 131735290, compound → HCID 131735291, compound

HRID 627218Notes

Reaction equation

HRID 627218 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([NH:16]C(=O)OC(C)(C)C)[C:11]([CH2:14][CH3:15])=[CH:12][CH3:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si](OC[C@@H](NC(=O)OC(C)(C)C)/C(/CC)=C/C)(C(C)(C)C)(C)C>C(Cl)Cl.[Br-].[Zn+2].[Br-]>[Si:1]([O:8][CH2:9][C@@H:10]([NH2:16])[C:11]([CH2:14][CH3:15])=[CH:12][CH3:13])([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 131735290HCID 131735290, compoundHCID 131735292HCID 131735292, compound

Product 1

HCID 131735291HCID 131735291, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)-3-ethylpent-3-en-2-ylcarbamate (Intermediate 203, 17.2 g, 50.06 mmol) in DCM (300 mL) at room temperature was added zinc bromide (45.1 g, 200.25 mmol). The reaction mixture was stirred for 2 days. The reaction mixture was filtered through fitted funnel and washed with saturated sodium bicarbonate. The aqueous layer was extracted two more times with DCM and the organics were combined, dried over magnesium sulfate, filtered and concentrated to afford the title compound (12.19 g, 100%) as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthrough fitted funnel
  3. washwashed with saturated sodium bicarbonate
  4. extractionThe aqueous layer was extracted two more times with DCM
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2aed7a10ea704a84ab747ee04f0796a9
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

Loading…