Triethylamine → HCID 69733477, compound

HRID 1274535Notes

Reaction equation

HRID 1274535 reaction equation
Cl.NC[C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:14])[CH:5]=1.[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][C:5]1[C:6]([OH:14])=[C:7]([CH:12]=[CH:13][CH:4]=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 69733477HCID 69733477, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-aminomethyl-2-hydroxybenzoate 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--2-hydroxybenzoate (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-fa30785d320a48138b10fc8bb60009c4
Source dataset
uspto-grants-2000_12
Patent number
US06156884

Reaction notes

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