Triethylamine → HCID 178454995, compound

HRID 1728493Notes

Reaction equation

HRID 1728493 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-1db8b0b1812d4868baac3515eac2064d
Source dataset
uspto-grants-1994_07
Patent number
US05326863

Reaction notes

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