Water → HCID 131720052, compound

HRID 1684441Notes

Reaction equation

HRID 1684441 reaction equation
C(=O)([O-])O.[Na+].[N+]([C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1)([O-])=O.O.C(OCC)(=O)C.[NH:24]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:25]([C:38]([OH:40])=[O:39])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH:36]=[O:37])[CH:28]=1>>[NH:24]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[C@H:25]([C:38]([O:40][CH2:13][C:12]1[CH:15]=[CH:16][CH:9]=[CH:10][CH:11]=1)=[O:39])[CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([CH:36]=[O:37])[CH:28]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 660114-Nitrobenzyl bromideHCID 516892Sodium BicarbonateHCID 7017963Boc-Trp(For)-OH

Product 1

HCID 131720052HCID 131720052, compoundYield 47.7%

Procedure

In 5 mg of DMP was dissolved 0.33 g of t-Boc-Trp(CHO)-OH, 0.17 g of sodium hydrogen carbonate was added. The solution was then stirred. To the mixture was added 1.08 g (5 mmol) of p-nitrobenzyl bromide, and stirring was effected at room temperature for 24 hours. Water and ethyl acetate were added to the reaction solution. The mixture was shaken, and the organic layer was recovered and the solvent was evaporated. The residue was purified with a silica gel column (manufactured by Merck Co., Kieselgel 60, 50 g, elution with hexane:ethyl acetate=6:4), to obtain 0.2 g of t-Boc-Trp(CHO)-OBzl (NO2). The peptide was dissolved in 5 ml of DMF, 0.5 ml of piperidine was added thereto, and the mixture was stirred at 0° C. for 1.5 hours. The solvent was evaporated under reduced pressure, 0.5 ml of 98% formic acid was added thereto, and the mixture was stirred at room temperature for 4 hours. About 30 ml of ether was added to obtain a precipitate. The precipitate was filtered and dried to obtain 0.16 g of H-Trp-OBzl (NO2).

Workup

  1. additionwas added
  2. stirringstirring
  3. stirringThe mixture was shaken
  4. customthe organic layer was recovered
  5. customthe solvent was evaporated
  6. customThe residue was purified with a silica gel column (manufactured by Merck Co., Kieselgel 60, 50 g, elution with hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-d6d4b7f9b74a4ba884e431cc7e7590f4
Source dataset
uspto-grants-1997_06
Patent number
US05639860

Reaction notes

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