HCID 20139255, compound → HCID 14207580, compound

HRID 1252723Notes

Reaction equation

HRID 1252723 reaction equation
[CH:1]([O:4][C:5]([NH:7][C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:15]=[C:14]([CH3:26])[C:9]=1[C:10]([O:12]C)=[O:11])=[O:6])([CH3:3])[CH3:2]>[OH-].[Na+].COCCOC>[CH:1]([O:4][C:5]([NH:7][C:8]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:15]=[C:14]([CH3:26])[C:9]=1[C:10]([OH:12])=[O:11])=[O:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 20139255HCID 20139255, compound

Product 1

HCID 14207580HCID 14207580, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl 2-isopropoxycarbonylamino-4-benzyloxy-6-methyl-benzoate (171 mg, 0.000487 mol) in sodium hydroxide (4% solution, 10 ml) and 1,2-dimethoxyethane (10 ml) was refluxed for 4 hours and then left at room temperature overnight. The organic solvent was removed under reduced pressure, the aqueous extract was acidified to pH 3 with 5% hydrochloric acid. A white suspension was formed which was extracted with ethyl acetate. The ethyl acetate layer was dried over magnesium sulphate and evaporated to give a solid. This solid was further purified by column chromatography (50% ethyl acetate: pet. ether) to give 2-(isopropoxy)carbonylamino-4-benzyloxy-6-methyl-benzoic acid (97 mg), m.p. 137°-139° C., IR (CHCl3): 2500-3200, 1721, 1660, 1610, 1585, 1520 cm-1 ; H-NMR (acetone-d6): 1.9 (d, 6H, CH3CHCH3), 3.10 (s, 3H, Me), 5.4 (m, 1H, CH3CHCH3), 5.4 (s, 2H, PhCH2), 7.2 (m, 1H, ArH), 8.0 (m, 5H, Ph).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionthe aqueous extract
  3. customA white suspension was formed which
  4. extractionwas extracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulphate
  6. customevaporated
  7. customto give a solid
  8. customThis solid was further purified by column chromatography (50% ethyl acetate: pet. ether)

Sources & evidence

ORD record
ord-2ec4840e1966450caef85ead4246178d
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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