p-Bromobenzenesulfonyl chloride → HCID 54389295, compound

HRID 1292246Notes

Reaction equation

HRID 1292246 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[C:13]([O:17][C:18](=[O:24])[C@H:19]([CH:21]([CH3:23])[CH3:22])[NH2:20])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>O1CCCC1.Cl.C(OCC)(=O)C>[C:13]([O:17][C:18](=[O:24])[CH:19]([NH:20][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9])[CH:21]([CH3:22])[CH3:23])([CH3:15])([CH3:14])[CH3:16]

Participants

7

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 54389295HCID 54389295, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromobenzenesulfonyl chloride (20 g, 0.070 mol) and (L)-valine-tert-butyl ester, hydrochloride (16.4 g, 0.078 mol) in aqueous tetrahydrofuran (400 mL, 1:1) was added dropwise triethylamine (15.6 g, 0.15 mol). The reaction mixture was stirred at room temperature for 16 hours, then diluted with aqueous HCl (1M, 300 mL) and ethyl acetate (300 mL). The layers were separated and the organic portion was washed with brine, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo leaving a white solid. The crude product was recrystallized from hexane/ethyl acetate to give the title compound as white crystalline needles. Yield: 19.7 g (67%); mp 108°-110°;

Workup

  1. customThe layers were separated
  2. washthe organic portion was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customleaving a white solid
  7. customThe crude product was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-1c98207db52742b5a4c553743ee172ae
Source dataset
uspto-grants-1998_05
Patent number
US05756545

Reaction notes

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