Hydrochloric Acid → Z-Lys(Boc)-Phe-Phe-OH

HRID 746201

Reaction equation

HRID 746201 reaction equation
[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:2]([C:15]([OH:17])=O)[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.[NH2:29][C@H:30]([C:38]([NH:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(N1CCOCC1)C>CN(C)C=O>[NH:1]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C@H:2]([C:15]([NH:29][C@H:30]([C:38]([NH:40][C@H:41]([C:49]([OH:51])=[O:50])[CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:39])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:17])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 98765IN2-(benzyloxycarbonyl)-N6-(tert-butoxycarbonyl)-L-lysineHCID 6993090L-Phenylalanyl-L-phenylalanine

Product 1

HCID 131714787Z-Lys(Boc)-Phe-Phe-OH

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.19 g of Z-Lys(Boc)-OPc and 2.47 g of HCl.H-Phe-Phe-OH are taken up in 50 ml of dimethylformamide, 0.84 ml of N-ethylmorpholine are added and the whole is left to stand for 24 hours at 20°. The reaction mixture is concentrated by evaporation and the residue is triturated with water and dried over phosphorus pentoxide. Recrystallisation from ether yields crystals having a melting point of 154° to 156°.

Workup

  1. waitthe whole is left
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. customthe residue is triturated with water
  4. dry with materialdried over phosphorus pentoxide
  5. customRecrystallisation from ether
  6. customyields crystals

Sources & evidence

ORD record
ord-58f6271e8c0d42118b25fb5f5ea2c0ab
Source dataset
uspto-grants-1986_07
Patent number
US04603120

Linked notes

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