Water → Glycine, N-((2-acetyl-7-(phenylmethoxy)-4-benzofuranyl)sulfonyl)-

HRID 979206Notes

Reaction equation

HRID 979206 reaction equation
[C:1]([C:4]1[O:5][C:6]2[C:12]([OH:13])=[CH:11][CH:10]=[C:9]([S:14](=[O:21])(=[O:20])[NH:15][CH2:16][C:17]([OH:19])=[O:18])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.O>CN(C=O)C>[C:1]([C:4]1[O:5][C:6]2[C:12]([O:13][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:11][CH:10]=[C:9]([S:14](=[O:20])(=[O:21])[NH:15][CH2:16][C:17]([OH:19])=[O:18])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13851452HCID 13851452, compound

Product 1

HCID 3064772Glycine, N-((2-acetyl-7-(phenylmethoxy)-4-benzofuranyl)sulfonyl)-Yield 56.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the 7-hydroxy compound (1.8 g) obtained in Example 28 (Compound No. 28), K2CO3 (1.6 g) and benzylbromide (2.9 g) in DMF was stirred at 80° C. for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate, which was purified by a silica-gel column chromatography to give 1.3 g of 2-acetyl-4-(N-carboxymethylsulfamoyl)-7-benzyloxybenzofuran as yellow crystals. After the obtained product was added to 20 ml of 2N-NaOH aqueous solution and the mixture was stirred for 30 minutes, the resultant was acidified to form precipitate, which was recrystallized with ethanol to give 0.4 g of 2-acetyl-4-(N-carboxymethylsulfamoyl)-7-benzyloxybenzofuran. The physical constants are shown in Table 4.

Workup

  1. extractionextracted with ethyl acetate, which
  2. customwas purified by a silica-gel column chromatography

Sources & evidence

ORD record
ord-e04ca9457c2244d688378e2143a35af1
Source dataset
uspto-grants-1987_05
Patent number
US04666931

Reaction notes

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