Sodium Chloride → HCID 22877878, compound

HRID 1488849Notes

Reaction equation

HRID 1488849 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C([NH:41][C@H:42]([C:44]([NH2:46])=[O:45])[CH3:43])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[OH-].[Na+].[Cl-].[Na+]>CO>[NH2:1][C:2]1[CH:3]=[C:4](/[CH:10]=[CH:11]\[C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[NH2:41][C@H:42]([C:44]([NH2:46])=[O:45])[CH3:43]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 22877914HCID 22877914, compound

Product 1

HCID 22877878HCID 22877878, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One gram (1.6 mmols) of (Z)-1-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene-Fmoc-L-alanineamide was dissolved in 10 ml of methanol, and 0.9 ml (1.76 mmols) of an aqueous solution of 2-N sodium hydroxide were added thereto. The mixture was stirred for 3 hours. A saturated aqueous solution of sodium chloride was added thereto, and the resulting mixture was extracted three times with dichloromethane. The extract was dried over anhydrous sodium sulfate, and concentrated to dryness under reduced pressure. The product was purified using a silica-gel plate (mixture of 5-% by volume methanol and dichloromethane) to produce 543 mg of the final compound in a yield of 87.9%.

Workup

  1. extractionthe resulting mixture was extracted three times with dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. customThe product was purified
  5. additiona silica-gel plate (mixture of 5-% by volume methanol and dichloromethane)

Sources & evidence

ORD record
ord-548e0c024d0442089c014ce5294f8304
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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