Triethylamine → methyl N-tert-butoxycarbonylaminomethyl-salicylate

HRID 1457404Notes

Reaction equation

HRID 1457404 reaction equation
Cl.NC[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:15]([O:19][C:20]([O:22]C(OC(C)(C)C)=O)=O)([CH3:18])([CH3:17])[CH3:16].[CH2:30]([N:32](CC)CC)C>CO>[C:15]([O:19][C:20]([NH:32][CH2:30][O:14][C:6]1[C:7](=[CH:12][CH:13]=[CH:4][CH:5]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:22])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 22556073Methyl 4-aminomethylsalicylate hydrochloride

Product 1

HCID 54558375methyl N-tert-butoxycarbonylaminomethyl-salicylateYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-aminomethylsalicylate hydrochloride (10.9 g, 50 mmoles) was suspended in anhydrous methanol (200 mL) and di-tert-butyldicarbonate (10.9 g, 50 mmoles) and triethylamine (7.0 mL, 50 mmoles) were added. The solid rapidly dissolved with the slow evolution of gas. The reaction mixture was stirred at room temperature for 18 hours under dry nitrogen, then evaporated to dryness to afford a white amorphous mass. This mass was partitioned between ethyl acetate (200 mL) and water (100 mL). The layers were separated, and the ethyl acetate solution was dried over anhydrous sodium sulfate. The solution was filtered and evaporated to a white solid. This solid was crystallized from ethyl acetate/hexanes, filtered, and dried in vacuo to afford 13.7 g (97% yield) of methyl N-tert-butoxycarbonylaminomethyl-salicylate (m.p. 95°-96° C., open capillary, uncorrected).

Workup

  1. dissolutionThe solid rapidly dissolved with the slow evolution of gas
  2. customevaporated to dryness
  3. customto afford a white amorphous mass
  4. customThis mass was partitioned between ethyl acetate (200 mL) and water (100 mL)
  5. customThe layers were separated
  6. dry with materialthe ethyl acetate solution was dried over anhydrous sodium sulfate
  7. filtrationThe solution was filtered
  8. customevaporated to a white solid
  9. customThis solid was crystallized from ethyl acetate/hexanes
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-e2787e5fb90848bebaee82d99fc79b23
Source dataset
uspto-grants-1998_12
Patent number
US05847192

Reaction notes

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