Triethylamine → Boc-Lys(Z)-Glu(OBzl)OBzl

HRID 615276Notes

Reaction equation

HRID 615276 reaction equation
[NH2:1][C@H:2]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[NH:32]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:33]([C:49](ON1C(=O)CCC1=O)=[O:50])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40]>C(#N)C.O>[NH:32]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[C@H:33]([C:49]([NH:1][C@H:2]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:3][CH2:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:50])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3037947L-Glutamic acid dibenzyl esterHCID 12686578Boc-Lys(Z)-OSu

Product 1

HCID 13384852Boc-Lys(Z)-Glu(OBzl)OBzlYield 97.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

H-Glu(OBzl)OBzl (2.0 g) was dissolved in a mixture of acetonitrile (50 ml) and water (10 ml). The solution was cooled to 0° C. and triethylamine (400 mg) and Boc-Lys(Z)OSu (1.91 g) were added. The mixture was stirred at 0°-5° C. for 2 hours and at room temperature for 3 hours. The solvent was distilled off and the residue was poured into a mixture of ethyl acetate (100 ml) and 2.5% hydrochloric acid. The organic layer was washed with water (50 ml×2), 2.5% sodium hydrogen carbonate (50 ml) and water (50 ml×3) in that order and dried over magnesium sulfate. The solvent was then distilled off to give Boc-Lys(Z)-Glu(OBzl)OBzl (2.70 g).

Workup

  1. distillationThe solvent was distilled off
  2. additionthe residue was poured into a mixture of ethyl acetate (100 ml) and 2.5% hydrochloric acid
  3. washThe organic layer was washed with water (50 ml×2), 2.5% sodium hydrogen carbonate (50 ml) and water (50 ml×3) in that order
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-f00b66d60cb341bcb8b8f27fa9bd810d
Source dataset
uspto-grants-1985_02
Patent number
US04497801

Reaction notes

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