Water → HCID 18536179, compound

HRID 412186Notes

Reaction equation

HRID 412186 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=2)[CH:12]=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:24]N1C(=O)CCC1=O.O.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[Br:24][C:12]1[C:13]2[C:18](=[CH:17][C:16]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)[C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 18536093HCID 18536093, compound

Product 1

HCID 18536179HCID 18536179, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Step B, (2.05 g, 6.08 mmol) in acetic acid (50 mL) was added N-bromosuccinimide (1.14 g, 6.38 mmol) in one portion. The reaction mixture was stirred at ambient temperature for 2 hrs, then H2O (100 mL) and CH2Cl2 (100 mL) were added and the resulting mixture was cooled to 0° C. The aqueous layer was adjusted to pH of about 7 by addition of 10 N aqueous NaOH and the organic layer was extracted. The aqueous phase was extracted with a further portion of CH2Cl2 (100 mL), and the combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was triturated with 1:1 hexane-EtOAc to provide the titled product as a grey solid.

Workup

  1. temperaturethe resulting mixture was cooled to 0° C
  2. extractionthe organic layer was extracted
  3. extractionThe aqueous phase was extracted with a further portion of CH2Cl2 (100 mL)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with 1:1 hexane-EtOAc

Sources & evidence

ORD record
ord-801b5e1f4af04003b6f17905c065e134
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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