HCID 56777339, compound → HCID 178453394, compound

HRID 1731593Notes

Reaction equation

HRID 1731593 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].[NH:17]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@@H:18]([C:31](ON1C(=O)CCC1=O)=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C.CO>[NH:17]([C:41]([O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:42])[C@@H:18]([C:31]([NH:1][CH2:2][C:3]([NH:5][C@H:6]([C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4])=[O:32])[CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25]

Participants

5

Reactant 2

HCID 56777339HCID 56777339, compoundHCID 178512899HCID 178512899, compound

Product 1

HCID 178453394HCID 178453394, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

8.8 Grams (20 mM) of H-Gly-Arg-CHA.2HCl was dissolved in 21.5 ml of DMF, to this solution was added 5.1 ml (40 mM) of NEM. To the mixture was further added with 9.6 g (20 mM) of Z-D-Lys(BOC)-OSu and reacted at room temperature for 18 hours. After the reaction was completed, the DMF was removed by evaporation under a reduced pressure and the residue obtained was dissolved in MeOH and reprecipitated in 1 liter of AcOEt. The crystals precipitated were collected by filtration and dried to obtain 14.9 g (97.4%) of Z-D-Lys(BOC)-Gly-Arg-CHA.HCl. Rf1 =0.50. Melting point: 207.5° C. (decomposed). [α]D20 -8.0 (C=0.5, MeOH)

Workup

  1. additionwas added 5.1 ml (40 mM) of NEM
  2. customreacted at room temperature for 18 hours
  3. customthe DMF was removed by evaporation under a reduced pressure
  4. customthe residue obtained
  5. customreprecipitated in 1 liter of AcOEt
  6. customThe crystals precipitated
  7. filtrationwere collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-a661aea3d5a64df286b8d87595f5dee9
Source dataset
uspto-grants-1986_11
Patent number
US04622389

Reaction notes

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