4-Methylmorpholine → HCID 10695590, compound

HRID 1292244Notes

Reaction equation

HRID 1292244 reaction equation
Cl.[C:2]([O:6][C:7](=[O:13])[C@H:8]([CH:10]([CH3:12])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].CN1CCOCC1.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>ClCCl>[C:2]([O:6][C:7](=[O:13])[C@@H:8]([NH:9][S:34]([C:31]1[CH:30]=[CH:29][C:28]([C:25]2[CH:26]=[CH:27][C:22]([Br:21])=[CH:23][CH:24]=2)=[CH:33][CH:32]=1)(=[O:35])=[O:36])[CH:10]([CH3:11])[CH3:12])([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27568454'-Bromobiphenyl-4-sulfonyl chlorideHCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 10695590HCID 10695590, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-valine-tert-butyl ester hydrochloride (15.7 g, 0.075 mol) and N-methylmorpholine (15.2 g, 0.15 mol) in dichloromethane (250 mL) was added in one portion 4'-bromobiphenyl-4-sulfonyl chloride (25 g, 0.075 mol). The solution was stirred at room temperature for 16 hours, filtered, and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate (250 mL) and washed with HCl (1N), saturated sodium chloride, and dried over magnesium sulfate. The drying agent was filtered, and the filtrate was concentrated in vacuo leaving a cream-colored solid. The crude product was purified using silica gel chromatography (elution with chloroform) to give the title compound (21.2 g, 60%) as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate (250 mL)
  4. washwashed with HCl (1N), saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe drying agent was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customleaving a cream-colored solid
  9. customThe crude product was purified
  10. washsilica gel chromatography (elution with chloroform)

Sources & evidence

ORD record
ord-456d754cb7ac4bd28d00f449b0fea4ac
Source dataset
uspto-grants-1998_05
Patent number
US05756545

Reaction notes

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