Triethylamine → 8-(((Tert-butoxy)carbonyl)amino)octanoic acid

HRID 2198019Notes

Reaction equation

HRID 2198019 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[O:12](C(OC(C)(C)C)=O)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O.C(N(CC)CC)C>CO>[C:13]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660858-Aminooctanoic acidHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 5462158-(((Tert-butoxy)carbonyl)amino)octanoic acidYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

NH2—(CH2)7—COOH (5.00 g, 31.4 mmol), (BOC)2O (7.52 g, 34.5 mmol) and triethylamine (3.48 g, 34.5 mmol) were dissolved in 200 mL of methanol, and the mixture was stirred at 60° C. for 12 hours. After the reaction completed, methanol was removed under reduced pressure, and the obtained material was redissolved in 100 mL of ethyl acetate. Then, the resultant solution was subjected to separation using 0.2 mol/l HCl (twice) and water (twice), and dehydrating was carried out with anhydrous sodium sulfate. After that, recrystallization with hexane at 4° C. and collection using a glass filter (G6) were performed, thereby obtaining Boc-NH—(CH2)7—COOH (5.93 g, 22.9 mmol, yield: 73%).

Workup

  1. custommethanol was removed under reduced pressure
  2. dissolutionthe obtained material was redissolved in 100 mL of ethyl acetate
  3. customThen, the resultant solution was subjected to separation
  4. customAfter that, recrystallization with hexane at 4° C.
  5. customcollection
  6. filtrationfilter (G6)

Sources & evidence

ORD record
ord-1dcd9bb5299c426ea77b19a26bb93602
Source dataset
uspto-grants-2012_12
Patent number
US08338643B2

Reaction notes

Loading…