Sodium Hydroxide → HCID 22877877, compound

HRID 1488847Notes

Reaction equation

HRID 1488847 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][CH2:42][C:43]([NH2:45])=[O:44])(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.[OH-].[Na+].C(=O)([O-])O.[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][CH2:42][C:43]([NH2:45])=[O:44]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 22877916HCID 22877916, compound

Product 1

HCID 22877877HCID 22877877, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-1-(3-Amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-ethene-Fmoc-glycineamide (1.08 g, 1.82 mmols) was dissolved in 20 ml of methanol, and 1.0 ml (2.0 mmols) of a 2-N sodium hydroxide aqueous solution was added thereto. The mixture was stirred for 3 hours. A saturated solution of sodium hydrogencarbonate was added thereto, and the 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-% methanol and dichloromethane) to produce 479 mg of the final product in a yield of 70.7%.

Workup

  1. extractionthe 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-% methanol and dichloromethane)

Sources & evidence

ORD record
ord-194db4616cd648b291884625cc07498b
Source dataset
uspto-grants-1997_10
Patent number
US05674906

Reaction notes

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