Triethylamine → HCID 178454995, compound

HRID 2248006Notes

Reaction equation

HRID 2248006 reaction equation
[C:1]1([CH:7]=[CH:8][C@@H:9]2[NH:12][C:11](=[O:13])[C@H:10]2[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Si:49](Cl)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50]>CN(C=O)C>[C:1]1([CH:7]=[CH:8][C@@H:9]2[N:12]([Si:49]([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50])[C:11](=[O:13])[C@H:10]2[CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]([NH:31][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[N:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 178523910HCID 178523910, compound

Product 1

HCID 178454995HCID 178454995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. DMF (25 mL) solution of compound 33 (6.8 g, 12.3 mmol) was added triethylamine (2.05 g, 20 mmol) and tert-butyldimethylsilyl chloride (3.05 g, 20 mmol). The reaction mixture was warmed to room temperature and stirred for 1.5 h. The suspension was partitioned between Et2O and pH 7.0 aqueous buffer. The organic layer was dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography to afford 8.4 g (quantitative) of the title product.

Workup

  1. customTo a 0° C
  2. customThe suspension was partitioned between Et2O and pH 7.0 aqueous buffer
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-786c00125af547b4b42e8f48c084bfec
Source dataset
uspto-grants-1991_08
Patent number
US05037819

Reaction notes

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