Triethylamine → 2,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl ester

HRID 383199

Reaction equation

HRID 383199 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:13])[C@H:6]([CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[NH2:7].C(N([CH2:19][CH3:20])CC)C.[CH2:21]([O:28][CH2:29][C:30](Cl)=[O:31])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)(=O)C>[CH3:3][O:4][C:5](=[O:13])[CH:6]([NH:7][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:20]1[CH:19]=[CH:24][CH:23]=[CH:22][CH:27]=1)[CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:30](=[O:31])[CH2:29][O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117778Methyl L-lysinate dihydrochlorideHCID 177085Benzyloxyacetyl chloride

Product 1

HCID 596824872,6-Bis-(2-benzyloxy-acetylamino)-hexanoic acid methyl esterYield 31.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of L-lysine methyl ester dihydrochloride (50 grams, 214.4 mmol), triethylamine (131 grams, 1.294 moles) in ethyl acetate (750 mL) at room temperature was added benzyloxy acetyl chloride (120 grams, 650.4 mmol) drop wise. The mixture was further stirred at room temperature for 2 hours. The solids were filtered off. The organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL), dried over sodium sulphate and distilled. The crude 2 was purified by column chromatography on silica gel using Benzene: Ethyl acetate (9:1) to get pure 2 (30 grams, 31.8%) as a white powder.

Workup

  1. filtrationThe solids were filtered off
  2. washThe organic phase was washed with 5% sodium bicarbonate (2×100 mL), water (2×100 mL)
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled
  5. customThe crude 2 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-eafcc244dfa248c5ba85114b659eccac
Source dataset
uspto-grants-2013_02
Patent number
US08367108B2

Linked notes

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