Diisopropylethylamine → HCID 23501809, compound

HRID 1835606Notes

Reaction equation

HRID 1835606 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[C:17]([O:21][C:22]([NH:24][CH:25](N)[CH2:26][CH2:27][NH2:28])=[O:23])([CH3:20])([CH3:19])[CH3:18].O[C:31]1C2N=NNC=2C=CC=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>O.CN(C=O)C>[C:17]([O:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][NH:28][C:14](=[O:16])[C:12]([NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH3:13])[CH3:31])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 736104N-carbobenzyloxyalanineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23501800HCID 23501800, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 23501809HCID 23501809, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N-carbobenzyloxyalanine (1.3 g, 5.7 mmol), 3-(N-tertbutoxycarbonylamino)-1,3-propanediamine (1 g, 5.7 mmol), hydroxybenzotriazole (0.88 g, 5.8 mmol), HBTU (2.4 g, 0.63 mmol), and diisopropylethylamine (1.48 g, 11.5 mmol) were added to dry DMF (25 mL) under nitrogen and stirred 16 hours, when the reaction was poured into water (100 mL) and extracted with ethyl acetate. The combined organics were washed with 0.1N HCl and saturated bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The reaction mixture was not further purified but carried directly into the next step. Mass Spec (EI): m/z=380.3 (M+H)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with 0.1N HCl and saturated bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe reaction mixture was not further purified

Sources & evidence

ORD record
ord-f7c164d637f14d89be1aebdc193353ce
Source dataset
uspto-grants-2004_08
Patent number
US06770259B2

Reaction notes

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