Diisopropylamine → HCID 59784094, compound

HRID 2079772Notes

Reaction equation

HRID 2079772 reaction equation
CN([C@@H](C)C([NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][C@H:21]1[C:26]([NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:27])=[O:19])[CH:15]([CH3:17])[CH3:16])=O)C(=O)OC(C)(C)C.[CH:40](NC(C)C)(C)C.[C:47](N[C@H](C(O)=O)C(C)C)([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48].CN(C(ON1N=N[C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][C:71]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O.CN(C=O)C>[C:50]([O:49][C:47](=[O:48])[NH:13][C@H:14]([C:18]([N:20]1[CH2:25][CH2:24][N:23]([CH2:40][C:71]2[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=2)[CH2:22][C@H:21]1[C:26](=[O:27])[NH:28][C@H:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:32][CH2:31][CH2:30]1)=[O:19])[CH:15]([CH3:17])[CH3:16])([CH3:51])([CH3:52])[CH3:53]

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59784098HCID 59784098, compound

Product 1

HCID 59784094HCID 59784094, compoundYield 119.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous DMF (11 ml) is added to a 100 ml round bottom flask containing compound 7 (190 mg, 0.544 mmol) under N2. After ten minutes diisopropylamine (0.473 ml, 2.72 mmol) is added to the flask. It is then stirred at room temperature for 1 hr. Boc-L-valine (118.19 mg, 0.544 mmol) is then added to the flask and stirred for 1 hr. HBTU (227 mg, 0.598 mmol) is added to the reaction followed by HOBT (81.6 mg, 0.604 mmol). The reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS shows completion of the reaction. It is then diluted with EtOAc and washed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to yield 356 mg (>100%) of the desired product 9.

Workup

  1. stirringstirred for 1 hr
  2. stirringThe reaction mixture is then stirred at room temperature under N2 overnight at which point LCMS
  3. customcompletion of the reaction
  4. washwashed subsequently with 1.0 M citric acid, brine, saturated sodiumbicarbonate, brine, water and brine
  5. dry with materialThe organic layer is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-073dfeb82f2d48209acde2e2d1b516bc
Source dataset
uspto-grants-2011_04
Patent number
US07932255B2

Reaction notes

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