Dimethylformamide → Z-D-Lys(Boc)-Phe-Gly

HRID 2309822Notes

Reaction equation

HRID 2309822 reaction equation
C1C=C2C(N(O)N=NC2=CC=1)=[O:8].C1CCC(N=C=[N:21][CH:22]2CCCCC2)CC1.[NH:28]([C:56]([O:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)=[O:57])[C@@H:29]([C:42]([NH:44][C@H:45]([C:53](O)=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36].CN([CH:69]=[O:70])C>>[NH:28]([C:56]([O:58][CH2:59][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1)=[O:57])[C@@H:29]([C:42]([NH:44][C@H:45]([C:53]([NH:21][CH2:22][C:69]([OH:70])=[O:8])=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 13753067HCID 13753067, compound

Product 1

HCID 131715271Z-D-Lys(Boc)-Phe-Gly

Procedure

1.26 g of G-Gly-OMe.HCl, 1.6 g of HOObt, 1.3 ml of NEM and 2.2 g of DCC are added in succession, with stirring, to 5.3 g of Z-D-Lys(Boc)-Phe-OH (Example 1d) in 60 ml of DMF. After the mixture has been left to stand overnight, the urea is filtered off and the filtrate is concentrated in vacuo. The residue is taken up in 200 ml of ethyl acetate and the solution is washed in the cold with 10% strength citric acid solution, saturated sodium bicarbonate solution and water and concentrated in vacuo to about 40 ml, and ether/petroleum ether 1:1 are added to the residue. The precipitate is filtered off, washed with ether/petroleum ether 1:1 and dried.

Workup

  1. waitAfter the mixture has been left
  2. filtrationthe urea is filtered off
  3. concentrationthe filtrate is concentrated in vacuo
  4. washthe solution is washed in the cold with 10% strength citric acid solution, saturated sodium bicarbonate solution and water
  5. concentrationconcentrated in vacuo to about 40 ml, and ether/petroleum ether 1:1
  6. additionare added to the residue
  7. filtrationThe precipitate is filtered off
  8. washwashed with ether/petroleum ether 1:1
  9. customdried

Sources & evidence

ORD record
ord-4a0cc7af707a45e686f4663e10a45008
Source dataset
uspto-grants-1987_09
Patent number
US04696913

Reaction notes

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