Hydrochloric Acid → HCID 23385747, compound

HRID 1282533Notes

Reaction equation

HRID 1282533 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:27]([OH:29])=[O:28])[CH2:13][CH2:14][CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][CH:21]=2)(=[O:19])=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH2:39]Br)=[CH:37][CH:36]=1.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:27]([OH:29])=[O:28])[CH2:13][CH2:14][CH2:15][N:16]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([Br:26])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:39][C:38]2[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 23385746HCID 23385746, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23385747HCID 23385747, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of Nα,Nδ-di-(4-bromobenzenesulfonyl)-L-ornithine (145 mg, 0.25 mmol) in DMF (2.5 mL) was added NaH. The reaction was stirred at room temperature until the hydrogen evolution stoped. 4-fluorobenzyl bromide (57 mg, 0.3 mmol) in solution in DMF (0.5 mL) was added and the mixture was allowed to stirr at room temperature for 1 h. HCl (1N) was added until acidic pH (˜3) and the reaction was extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The crude material was purified by flash chromatography eluting with hexanes:EtOAc:AcOH, 50:50:00; 25:75:00 and then 25:70:0.5 to afford 142 mg (84%) of the title compound.

Workup

  1. extractionthe reaction was extracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude material was purified by flash chromatography
  5. washeluting with hexanes

Sources & evidence

ORD record
ord-d0b0abd44f1746adb4d0536beb93b625
Source dataset
uspto-grants-2002_09
Patent number
US06455587B1

Reaction notes

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