Acetic Acid → HCID 131731169, compound

HRID 474180Notes

Reaction equation

HRID 474180 reaction equation
[NH2:1][C@H:2]([C:15]([NH:17][C@H:18]([C:31]([OH:33])=O)[CH2:19][CH2:20][C:21](=[O:30])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(Cl)(Cl)Cl.CO.CC(O)=O>N1C=CC=CC=1>[NH:1]1[C:31](=[O:33])[C@H:18]([CH2:19][CH2:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:17][C:15](=[O:16])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 6212ChloroformHCID 131731167H-L-Lys(Boc)-L-Glu(OBzl)-OH

Product 1

HCID 131731169HCID 131731169, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

H-L-Lys(Boc)-L-Glu(OBzl)-OH (23.0, 0.05 mol) was dissolved in 100 ml of pyridine and refluxed for 4 hours. The reaction was monitored by TLC using the system of CHCl3:MeOH: 32% AcOH=5:3:1. After completion of the reaction, the mixture was evaporated in vacuum and 500 ml of 0.1% AcOH was added. The cyclo-L-Lys(Boc)-L-Glu(OBzl) was precipitated. The precipitate was filtered off, washed with water and dried in a vacuum oven at 40° C. The yield was 20.9 (86%). Rf=0.75 (CHCl3:MeOH: 32% AcOH=5:3:1); HPLC data: retention time 19.2 min.

Workup

  1. temperaturerefluxed for 4 hours
  2. customAfter completion of the reaction
  3. customthe mixture was evaporated in vacuum and 500 ml of 0.1% AcOH
  4. additionwas added
  5. customThe cyclo-L-Lys(Boc)-L-Glu(OBzl) was precipitated
  6. filtrationThe precipitate was filtered off
  7. washwashed with water
  8. customdried in a vacuum oven at 40° C

Sources & evidence

ORD record
ord-fe6e38eafeea432089e5235a26b98a6e
Source dataset
uspto-grants-2014_01
Patent number
US08637521B2

Reaction notes

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