Diethylamine → HCID 131730129, compound

HRID 539507Notes

Reaction equation

HRID 539507 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:2]([C:5]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:6])[CH2:3][NH2:4].C(NCC)C>C(Cl)Cl>[NH2:1][C@H:2]([C:5]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:6])[CH2:3][NH2:4]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 131730130HCID 131730130, compound

Product 1

HCID 131730129HCID 131730129, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 1-L round bottom flask is charged with Fmoc-Dap-Z, CH2Cl2 (122 mL) and diethylamine (61 mL, Acros). The solution is stirred at room temperature and the completion monitored by HPLC. After 7h, the mixture is concentrated (bath temp. <30° C.). The residue is suspended in CH2Cl2 (300 mL) and concentrated. This is repeated twice. To the residue is added MeOH (20 mL) and CH2Cl2 (300 mL), and the solution is concentrated. The residue is suspended in CH2Cl2 (100 mL) and toluene (400 mL), concentrated, and the residue left under vacuum overnight to give product.

Workup

  1. concentrationAfter 7h, the mixture is concentrated (bath temp. <30° C.)
  2. concentrationconcentrated
  3. additionTo the residue is added MeOH (20 mL) and CH2Cl2 (300 mL)
  4. concentrationthe solution is concentrated
  5. concentrationtoluene (400 mL), concentrated
  6. customto give product

Sources & evidence

ORD record
ord-84b00494196d4359938d84111d84b1bc
Source dataset
uspto-grants-2014_10
Patent number
US08871720B2

Reaction notes

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