Diethylamine → HCID 131719043, compound

HRID 1647910Notes

Reaction equation

HRID 1647910 reaction equation
[NH:1](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H:2]([C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:30][CH:29]=1)=[O:24])[CH2:17][O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(NCC)C>CN(C)C=O>[NH2:1][C@@H:2]([C:13]([NH:15][C@H:16]([C:23]([NH:25][C@H:26]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[CH:30][CH:29]=1)=[O:24])[CH2:17][O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 131719044HCID 131719044, compound

Product 1

HCID 131719043HCID 131719043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

93.0 g (about 102 mmol) of Fmoc-D-Trp-Ser(tBu)-Tyr(tBu)-OtBu are dissolved in 500 ml of dimethylformamide. 114.5 ml of diethylamine are added to this while stirring, reaction is allowed to take place at room temperature for 10 minutes, and the mixture is concentrated under high vacuum. The residue is triturated 3 times with petroleum ether and twice with diethyl ether. The diethyl ether is removed by distillation and then partition between ethyl acetate and water is carried out. The ethyl acetate is, after drying over Na2SO4, removed by distillation, and the residue is triturated twice with diethyl ether.

Workup

  1. customreaction
  2. customat room temperature
  3. customfor 10 minutes
  4. concentrationthe mixture is concentrated under high vacuum
  5. customThe residue is triturated 3 times with petroleum ether
  6. customThe diethyl ether is removed by distillation
  7. custompartition between ethyl acetate and water
  8. dry with materialafter drying over Na2SO4
  9. customremoved by distillation
  10. customthe residue is triturated twice with diethyl ether

Sources & evidence

ORD record
ord-d7b1e4d9cab4445199cdf1b93c953342
Source dataset
uspto-grants-1995_07
Patent number
US05434138

Reaction notes

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