Sodium Chloride → HCID 22877891, compound

HRID 1488853Notes

Reaction equation

HRID 1488853 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:45]([NH2:47])=[O:46])[CH2:43][OH:44])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[OH-].[Na+].[Cl-].[Na+]>CO.ClCCl>[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:45]([NH2:47])=[O:46])[CH2:43][OH:44]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 22877918HCID 22877918, compound

Product 1

HCID 22877891HCID 22877891, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(Z)-1-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene-Fmoc-L-serineamide (1.04 g, 1.56 mmols) was dissolved in 10 ml of methanol and 10 ml of dichloromethane, and 1.7 ml (3.4 mmols) of an aqueous solution of 2-N sodium hydroxide were added thereto. The mixture was stirred at room temperature for 24 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 315 mg of the final compound in a yield of 50.2%.

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-a6872ad0623d4948b33828b1a8306796
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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