Water → HCID 178512881, compound

HRID 1482154Notes

Reaction equation

HRID 1482154 reaction equation
O.[NH2:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:10])[NH2:9].[NH:14]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@H:15]([C:26](ON1C(=O)CCC1=O)=[O:27])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1>CN(C=O)C>[NH:14]([C:36]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:37])[C@H:15]([C:26]([NH:2][C@H:3]([C:11]([OH:13])=[O:12])[CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:9])[NH2:10])=[O:27])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11048356Z-Trp-OSuHCID 178418600HCID 178418600, compound2×

Product 1

HCID 178512881HCID 178512881, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.00 equivalents water and 1 equivalent Arg (Mw=174.2) were mixed with DMF and stirred at room temperature until a solution was obtained. 1.03 equivalents of Z-Trp-OSu (Mw=435.45; purity=98%) were dissolved in DMF and poured in the arginine solution. Stirring was then continued at room temperature for at least 5 hours. After checking the termination of the reaction by HPLC, the reaction mixture was precipitated by adding slowly cold acetonitrile (0±5° C.) and kept at this temperature for at least 30 minutes before filtration. The precipitate was washed 3 times with a mixture of CH3CN/IPE(Isopropylether) (1/1) and then 2 times with IPE. The solid was then dried in vacuo at 45° C. A white solid was finally obtained.

Workup

  1. customwas obtained
  2. stirringStirring
  3. waitwas then continued at room temperature for at least 5 hours
  4. customthe termination of the reaction by HPLC
  5. customthe reaction mixture was precipitated
  6. additionby adding slowly cold acetonitrile (0±5° C.)
  7. filtrationkept at this temperature for at least 30 minutes before filtration
  8. washThe precipitate was washed 3 times
  9. additionwith a mixture of CH3CN/IPE(Isopropylether) (1/1)
  10. customThe solid was then dried in vacuo at 45° C
  11. customA white solid was finally obtained

Sources & evidence

ORD record
ord-4be2caa784d948b8b9ce7e6b4f18c619
Source dataset
uspto-grants-2016_08
Patent number
US09409946B2

Reaction notes

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