Diisopropylethylamine → methyl N-(benzyloxycarbonyl)4-aminomethylsalicylate

HRID 363154Notes

Reaction equation

HRID 363154 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:14])[C:7](=[CH:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9].C(N(CC)C(C)C)(C)C.[CH2:24]([O:31][C:32](ON1C(=O)CCC1=O)=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)(Cl)Cl>[CH2:24]([O:31][C:32]([NH:2][CH2:3][C:4]1[CH:5]=[C:6]([OH:14])[C:7](=[CH:12][CH:13]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:33])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 22556073Methyl 4-aminomethylsalicylate hydrochloride

Product 1

HCID 54246052methyl N-(benzyloxycarbonyl)4-aminomethylsalicylateYield 84.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 4-aminomethylsalicylate hydrochloride (5.04 g 23.2 mmoles) was suspended in chloroform (80 mL) and N,N-diisopropylethylamine (4.10 mL, 23.5 mmoles) and N-(benzyloxycarbonyloxy)succinimide (6.48 g, 26.0 mmoles) were added. The reaction mixture was stirred at room temperature for 4 hours, during which time all solids dissolved. The reaction mixture was then extracted with 1N aqueous hydrochloric acid (100 mL), water (75 mL), and saturated aqueous sodium chloride (50 mL). The chloroform solution was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness to give a white solid. The product was crystallized from ethyl acetate:hexanes to afford 6.17 g (84% yield) of methyl N-(benzyloxycarbonyl)-4-aminomethylsalicylate (m.p. 91°-92° C., open capillary, uncorrected).

Workup

  1. dissolutiondissolved
  2. extractionThe reaction mixture was then extracted with 1N aqueous hydrochloric acid (100 mL), water (75 mL), and saturated aqueous sodium chloride (50 mL)
  3. dry with materialThe chloroform solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto give a white solid
  7. customThe product was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-13a6bc4ac76c4cd3a926b18604da13b1
Source dataset
uspto-grants-1999_02
Patent number
US05872224

Reaction notes

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