Diethylamine → HCID 131730129, compound

HRID 1797880Notes

Reaction equation

HRID 1797880 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 7 hours, 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. concentrationthe 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. waitthe residue left under vacuum overnight
  7. customto give product

Sources & evidence

ORD record
ord-ada1f94356914d2881663edc4805da97
Source dataset
uspto-grants-2013_01
Patent number
US08343928B2

Reaction notes

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