Sodium Hydroxide → HCID 19004497, compound

HRID 2225809Notes

Reaction equation

HRID 2225809 reaction equation
C[O:2][C:3](=[O:25])[C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([NH:15][CH:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH:16]1([NH:15][C:13](=[O:14])[CH2:12][O:11][C:8]2[CH:7]=[CH:6][C:5]([C:4](=[O:24])[C:3]([OH:25])=[O:2])=[CH:10][CH:9]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54288573HCID 54288573, compound

Product 1

HCID 19004497HCID 19004497, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[2-(cyclooctylamino)-2-oxoethoxy]-alpha-oxobenzeneacetic acid methyl ester (0.4 g) in methanol (40 mL) was treated with 1N sodium hydroxide solution (1.3 mL), and the mixture was stirred at room temperature for 15 minutes. After the solvents were evaporated under reduced pressure, water (20 mL) was added and the solution was acidified with 3N hydrochloric acid, then the aqueous layer was extracted with a mixture of dichloromethane-tetrahydrofuran (30 mL; 2:1). The organic layer was dried (MgSO4), evaporated and the resulting oil was crystallized from diethyl ether-hexane to yield 0.084 g of 4-[2-(cyclooctylamino)-2-oxoethoxy]-alpha-oxobenzeneacetic acid, mp 139°-140 ° C.

Workup

  1. customAfter the solvents were evaporated under reduced pressure, water (20 mL)
  2. additionwas added
  3. extractionthe aqueous layer was extracted with a mixture of dichloromethane-tetrahydrofuran (30 mL; 2:1)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated
  6. customthe resulting oil was crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-f2f20167ecbc496487137a17998ae789
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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