Diisopropylethylamine → HCID 44550117, compound

HRID 1924373Notes

Reaction equation

HRID 1924373 reaction equation
[Cl-].[CH3:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=[CH2:23])[CH:20]=3)[CH:15]=[CH:14][N:13]=2)[CH2:8][NH2+:7]1)=[O:5].[NH:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:25]([C:29](O)=[O:30])[CH:26]([CH3:28])[CH3:27].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[C:35]([O:34][C:32]([NH:24][C@H:25]([C:29]([N:7]1[CH2:8][C@H:9]([O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=[CH2:23])[CH:20]=3)[CH:15]=[CH:14][N:13]=2)[CH2:10][C@H:6]1[C:4]([O:3][CH3:2])=[O:5])=[O:30])[CH:26]([CH3:27])[CH3:28])=[O:33])([CH3:37])([CH3:38])[CH3:36]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 83693Boc-L-ValineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86635050HCID 86635050, compound

Product 1

HCID 44550117HCID 44550117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Intermediate 1 in DMF was added Boc-(L)-Val (1.05 eq), followed by iPr2NEt (3.5 eq) and TBTU (1.05 eq). The resulting reaction mixture was stirred 12 h at RT and partitioned between EtOAc and 1N aq. HCl. The organic layer was further washed with sat. aq. NaHCO3, brine, dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by SiO2 gel chromatography (hexane/EtOAc=7/3) to give the title compound as a colourless oil. MS (ES+) C27H35N3O6 requires: 497. Found: 498 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. custompartitioned between EtOAc and 1N aq. HCl
  3. washThe organic layer was further washed with sat. aq. NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by SiO2 gel chromatography (hexane/EtOAc=7/3)

Sources & evidence

ORD record
ord-6af3de9a87dd4bae96ef8393368673fc
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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