Diisopropylethylamine → HCID 117739360, compound

HRID 708895Notes

Reaction equation

HRID 708895 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([CH2:11][NH:12][CH3:13])[C:3]=1[OH:14].CCN(C(C)C)C(C)C.[CH2:24]([O:31][C:32]([O:34]N1C(=O)CCC1=O)=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[F:1][C:2]1[C:3]([OH:14])=[C:4]([CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1)[CH2:11][N:12]([CH3:13])[C:32](=[O:34])[O:31][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 91619139HCID 91619139, compound

Product 1

HCID 117739360HCID 117739360, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask containing 27A (1.6 g, 7.99 mmol), DIEA (2.088 ml, 11.99 mmol) in DMF (10 ml), was added N-(benzyloxycarbonyloxy) succinimide (2.19 g, 8.79 mmol). The mixture was stirred at rt for 1 h. The reaction was quenched with H2O and then extracted with EtOAc (3×). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude was purified by flash column chromatography (0-60% EtOAc/hexanes) to give 27B (1.8 g, 5.38 mmol, 67.4% yield). MS (ESI) m/z: 335.2 (M+H)+.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude was purified by flash column chromatography (0-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fedc606076944e7fbe3d6e1825146afc
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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