4-Methylmorpholine → Boc-Leu-Glu-OtBu

HRID 32338

Reaction equation

HRID 32338 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:7]([O:9]N1C(=O)CCC1=O)=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:24][C@H:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:27][C:28](=[O:30])[OH:29].CN1CCOCC1>CN(C=O)C.CN(C1C=CN=CC=1)C>[NH:1]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C@H:2]([C:7]([NH:24][C@H:25]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:26][CH2:27][C:28](=[O:29])[OH:30])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamateHCID 11023929Boc-Leu-OSu

Product 1

HCID 87984260Boc-Leu-Glu-OtBu

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of Boc-Leu-OSu and Glu-OtBu in DMF was added NMM and DMAP. The solution was stirred at ambient temperatures for 18 hours then the solvent was removed. Crude product was taken up in 100 ml CHCl3, washed 3× with pH 3 water (100 ml), once with water (100 ml) and once with brine (100 ml). Organic layer was dried with MgSO4 and filtered. Solvent was removed and solid was dried over vacuum. Solid was collected as a white powder (8.78 g, quant. yield, ˜80% purity TLC). Product was used directly without further characterization.

Workup

  1. customthe solvent was removed
  2. washwashed 3× with pH 3 water (100 ml)
  3. dry with materialOrganic layer was dried with MgSO4
  4. filtrationfiltered
  5. customSolvent was removed
  6. customsolid was dried over vacuum
  7. customSolid was collected as a white powder (8.78 g, quant. yield, ˜80% purity TLC)

Sources & evidence

ORD record
ord-a4465bcbca00476b927678186da410d5
Source dataset
uspto-grants-2008_09
Patent number
US07427600B2

Linked notes

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