Triethylamine → Z-Lys(Boc)-Lys(Boc)-OMe

HRID 328755Notes

Reaction equation

HRID 328755 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:19])[C@H:5]([CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[NH2:6].C(N(CC)CC)C.[NH:27]([C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52])[C@H:28]([C:41](ON1C(=O)CCC1=O)=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CN(C)C=O>[NH:27]([C:51]([O:53][CH2:54][C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:52])[C@H:28]([C:41]([NH:6][C@H:5]([C:4]([O:3][CH3:2])=[O:19])[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])=[O:42])[CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10939726Z-Lys(boc)-osuHCID 16218818L-Lysine, N6-[(1,1-dimethylethoxy)carbonyl]-, methyl ester, hydrochloride (1:1)

Product 1

HCID 59070592Z-Lys(Boc)-Lys(Boc)-OMe

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of Nε -t-butyloxycarbonyl-L-lysine methyl ester hydrochloride (H-Lys(Boc)-OMe.HCl) (0.89 g, 3 mmoles) and triethylamine (0.46 ml, 3.3 mmoles) in dimethyl-formamide (8 ml) is added Nα -benzyloxycarbonyl-Nε -t-butyloxy-carbonyl-L-lysine N-hydroxysuccinimide ester (Z-Lys(Boc)-OSu) (1.43 g, 3 mmoles) (Bull. Chem. Soc. Japan 39, 882 (1966)) and the mixture is allowed to stand at 4° C overnight followed by evaporation in vacuo at a bath temperature of 40° C. The residue is dissolved in ethyl acetate and the solution is washed successively with ice-cold M hydrochloric acid, water, and M sodium bicarbonate, dried over magensium sulfate and evaporated in vacuo to give a residue, which is precipitated from ethyl acetate-petroleum ether. Reprecipitation from the same solvent yields the desired product in pure form; yield 1.80 g (96.5%), [α]D22.5 -11.7°±0.5° (c 1.0, methanol). Thin-layer chromatography (silica gel): homogeneous (to ninhydrin after pretreatment with hydrobromic acid) in chloroform-methanol-acetic acid (90:10:3, v/v).

Workup

  1. customfollowed by evaporation in vacuo at a bath temperature of 40° C
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washthe solution is washed successively with ice-cold M hydrochloric acid, water, and M sodium bicarbonate
  4. dry with materialdried over magensium sulfate
  5. customevaporated in vacuo
  6. customto give a residue, which
  7. customis precipitated from ethyl acetate-petroleum ether
  8. customReprecipitation from the same solvent

Sources & evidence

ORD record
ord-739a9a32ccb04bd8b4d7911d795666b7
Source dataset
uspto-grants-1977_04
Patent number
US04018753

Reaction notes

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