Dimethylformamide → HCID 131726438, compound

HRID 1160176Notes

Reaction equation

HRID 1160176 reaction equation
[NH:1]([C:23]([O:25][CH2:26][CH:27]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33]2[C:28]1=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH3:11])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].CN(C=O)C.[CH2:45](Br)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[NH:1]([C:23]([O:25][CH2:26][CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:34]2[C:39]1=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:24])[C@H:2]([C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:20]([O:22][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:21])[CH2:16][CH:17]([CH3:19])[CH3:18])=[O:13])[CH3:11])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 131726439HCID 131726439, compound

Product 1

HCID 131726438HCID 131726438, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The Fmoc-Met-Ala-Leu (SEQ ID NO: 3) is added into a round bottom flask with DMF and a magnetic stirrer. After the tripeptide is dissolved, benzyl bromide, followed by cesium carbonate, is added to the solution with stirring. The reaction mixture is stirred at room temperature for 1.5 hrs. Then, the reaction mixture is slowly poured into a flask with iced water. The precipitate is collected by suction filtration. The product, Fmoc-Met-Ala-Leu-OBn (SEQ ID NO: 3), is washed with water and placed in a vacuum desiccator.

Workup

  1. additionis added to the solution
  2. stirringThe reaction mixture is stirred at room temperature for 1.5 hrs
  3. filtrationThe precipitate is collected by suction filtration
  4. washThe product, Fmoc-Met-Ala-Leu-OBn (SEQ ID NO: 3), is washed with water

Sources & evidence

ORD record
ord-6d241c2a504e4afcab56382950c83f6e
Source dataset
uspto-grants-2010_10
Patent number
US07816317B2

Reaction notes

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