Diisopropylethylamine → HCID 87964453, compound

HRID 1820684Notes

Reaction equation

HRID 1820684 reaction equation
Cl.CN(C)CCCN=C=NCC.O.ON1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2N=N1.CO[CH:26]([NH:29]C1C=CC=CC=1)[C:27]#[N:28].[C:36]([O:40][C:41]([NH:43][C@H:44]([C:49]([OH:51])=O)[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)C(C)C)(C)C.CCCC(C)C.[C:67](OCC)(=[O:69])C>CN(C)C=O.O>[C:36]([O:40][C:41]([NH:43][C@H:44]([C:49]([NH:29][CH:26]([C:27]#[N:28])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[O:69][CH3:67])=[O:51])[CH2:45][CH:46]([CH3:47])[CH3:48])=[O:42])([CH3:37])([CH3:38])[CH3:39]

Participants

9

Reactant 6

HCID 81531DiisopropylethylamineHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21882781Isohexane ethyl acetateHCID 68980759HCID 68980759, compound

Product 1

HCID 87964453HCID 87964453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.9 g) and 1-hydroxybenzotriazole hydrate (2.0 g) were added to a solution of 2-methoxyphenylamino acetonitrile (2.0 g) and N-tert-butoxycarbonyl L-leucine (2.5 g) in N,N-dimethylformamide (20 ml) at room temperature followed by N,N-diisopropylethylamine (5.3 ml) and stirred at room temperature overnight. The mixture was diluted with water, extracted into ethyl acetate and dried (MgSO4). The solvent was removed under vacuum to leave an oil which was subjected to column chromatography on silica eluting with isohexane/ethyl acetate 2:1 to give a colourless oil (3.7 g).

Workup

  1. extractionextracted into ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed under vacuum
  4. customto leave an oil which

Sources & evidence

ORD record
ord-b3a75a72f11940d8bf4d0e16a04c1316
Source dataset
uspto-grants-2009_10
Patent number
US07605159B2

Reaction notes

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