Sodium Chloride → HCID 22877887, compound

HRID 1488851Notes

Reaction equation

HRID 1488851 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:47]([OH:49])=O)[CH2:43][CH:44]([CH3:46])[CH3:45])(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:47]([NH2:1])=[O:49])[CH2:43][CH:44]([CH3:46])[CH3:45]

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 86751377HCID 86751377, compound

Product 1

HCID 22877887HCID 22877887, compoundYield 163.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

One gram (1.54 mmols) of (Z)-1-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethene-Fmoc-L-leucine was dissolved in 10 ml of methanol and 10 ml of dichloromethane, and 0.9 ml (1.7 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 column (mixture of 10-% by volume methanol and dichloromethane) to produce 560 mg of the final compound in a yield of 84.9%.

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 column (mixture of 10-% by volume methanol and dichloromethane)

Sources & evidence

ORD record
ord-8880defa767c4aef8a28ec7bc4769962
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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