Diethylamine → HCID 58078467, compound

HRID 2367953Notes

Reaction equation

HRID 2367953 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:4]=1[CH2:5][O:6][C:7](=[O:34])[C@H:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH:9]C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.C(NCC)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:4]=1[CH2:5][O:6][C:7](=[O:34])[C@H:8]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[NH2:9]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 58078465HCID 58078465, compound

Product 1

HCID 58078467HCID 58078467, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 500-mL round-bottom flask was charged with Fmoc-L-phenylalanine-2,4-dimethoxybenzyl ester (26.00 g, 48.3 mmol), CH2Cl2 (150 mL) and diethylamine (75 mL, Acros). Mixture was stirred at room temperature and the completion monitored by HPLC. After 4 h, the mixture was concentrated (bath temp<30° C.). The residue was resuspended in CH2Cl2 (200 mL) and concentrated. This was repeated once. To the residue was added MeOH (20 mL), which caused the formation of a gel. This residue was diluted with CH2Cl2 (200 mL), concentrated and the cloudy oil left under vacuum overnight. The residue was suspended in CH2Cl2 (100 mL), then toluene (120 mL) was added. The mixture was concentrated and the residue left under vacuum overnight.

Workup

  1. concentrationthe mixture was concentrated (bath temp<30° C.)
  2. concentrationconcentrated
  3. additionTo the residue was added MeOH (20 mL), which
  4. additionThis residue was diluted with CH2Cl2 (200 mL)
  5. concentrationconcentrated
  6. waitthe cloudy oil left under vacuum overnight
  7. additiontoluene (120 mL) was added
  8. concentrationThe mixture was concentrated
  9. waitthe residue left under vacuum overnight

Sources & evidence

ORD record
ord-c4fb567402754c018025ee47a45ac88d
Source dataset
uspto-grants-2014_04
Patent number
US08703714B2

Reaction notes

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